THE TOTAL SYNTHESIS OF NATURAL PRODUCTS The Total Synthesis of Natural Products VOLUME Edited by John ApSimon Ottawa-Carleton Institute for Research and Graduate Studies in Chemistry and Department of Chemistry Carleton University, Ottawa A WILEY-INTERSCIENCE PUBLICATION JOHN WILEY & SONS NEWYORK CHICHESTER BRISBANE TORONTO SINGAPORE A NOTE TO THE READER This book has been electronically reproduced from digital information stored at John Wiley & Sons, Inc We are pleased that the use of this new technology will enable us to keep works of enduring scholarly value in print as long as there is a reasonable demand for them The content of this book is identical to previous printings In recognition of the importance of preserving what has been written, it is a policy of John Wiley & Sons, Inc., to have books of enduring value published in the United States printed on acid-free paper, and we exert our best efforts to that end Copyright 1992 by John Wiley & Sons, lnc All rights reserved Published simultaneously in Canada Reproduction or translation of any part of this work beyond that permitted by Section 107 or 108 of the 1976 United States Copyright Act without the permission of the copyright owner is unlawful Requests for permission or further information should be addressed to the Permissions Department, John Wiley & Sons, Inc Library of Congress Cataloging in Publication Data: The Total synthesis of natural products “A Wiley-Interscience publication.” Original imprint, v 1: New York: Wiley-Interscience, 1973 Includes bibliographical references and indexes I Chemistry, Organic-Synthesis, I ApSimon, John QD262.T655 1973 541l.2 72-4075 ISBN 0-471-03251-4 (v 1) ISBN 0-47 1-55 189-9 (v 9) 10 I Contributor to Volume Kenji Mori, Department of Agricultural Chemistry, The University of Tokyo, Tokyo, Japan V Preface This volume is a single author effort covering the massive amount of synthetic work associated with Insect Pheromone Chemistry for the period 1979 to 1990 Professor Mori has, once more, demonstrated in a masterful way his key position in this field I have been editor of this series since its inception in 1973 and, although I am convinced of its value to the discipline of organic synthesis, other responsibilities and interests have slowly intruded, to the state where I must regretfully pass on the onerous task of keeping the initiative alive to another editor Over the past 18 years, I have had the honor of working with many outstanding authors and scientists I thank you personally for this collaboration, friendship, and support JOHN APSIMON Oitawa, Canada November 1991 vii Contents The Synthesis of Insect Pheromones, 1979-1989 KENJIMORI Subject Index 523 Formula Index 533 ix The Total Synthesis of Natural Products, Volume9 Edited by John ApSlmon Copyright © 1992 by John Wiley & Sons, Inc The Synthesis of Insect Pheromones, 1979-1989 KENJI MORI Depar~menfof Agricultural Chemistry, The Universiry of Tokyo, Japan 10 11 12 13 14 15 16 Introduction, General Methods, Alkanes as Pheromones, Pheromone Hydrocarbon with a Terminal Double Bond, 15 Pheromone Alcohols and Acetates with an E-Double Bond, 18 Pheromone Hydrocarbons and Acetates with a Z-Double Bond, 25 Pheromone Alcohols and Acetates with a Conjugated Diene and Conjugated Enyne System, 37 Pheromones with a Nonconjugated Diene System, 66 Phcromones with a Triene or Tetraene System, 79 Pheromones with an Epoxy Ring, 85 Chiral Alcohols and Their Esters as Pheromones, 98 Pheromone Aldehydes, 130 Pheromone Ketones, 157 Acids and Esters as Pheromones, 200 Pheromone Lactones, 16 lsoprenoid Hydrocarbons as Pheromones, 273 The Synthesis of Insect Pheromones, 1979-1989 17 Isoprenoid Alcohols, Formate, Acetates, Propanoates, and Epoxide as Pheromones, 280 18 Isoprenoid Aldehydes, Ketones, Acids, Esters, and Lactones as Pheromones, 332 19 Oxygen Heterocycles (Excluding Epoxides, Lactones, Hemiacetals, and Acetals) as Pheromones, 367 20 Acetals as Pheromones, 381 21 Spiroacetals as Pheromones, 444 22 Nitrogen Heterocycles and Sulfur-Containing Compounds as Pheromones, 478 23 Conclusion, 484 Acknowledgments, 486 References 486 INTRODUCTION Since the appearance of the first edition of this chapter in Volume Four of this series,' a tremendous amount of work has been published in the field of pheromone synthesis Simple but unique structures that can frequently be seen among pheromone molecules became favorite targets of synthetic chemists to test their methodology and strategy in pursuit of simplicity, selectivity, and efficiency It is therefore very difficult to write a comprehensive review on pheromone synthesis However, it is the aim of this chapter to summarize almost all of the notable syntheses in the pheromone area published between April 1979 to February 1990 Thus, this chapter will be of service to those chemists who want a quick view of the existing synthetic methods for each of the individual pheromones The pheromones described in this chapter are classified according to the structural type, as in the first edition Because the synthesis of optically active pheromones is now a common practice, enantioselective synthesis has been included in each section instead of being made into an independent section, The relationships between absolute configuration and pheromone activity are briefly summarized at the end of this chapter There are a number of recent monographs and reviews on pheromones The following brief listing highlights the focus of literature published within the time frame of this chapter A monograph on all aspects of pheromone research-including isolation, structure determination, synthesis, and estimation of enantiomeric purity-was published in 1984.2 Synthetic methodologies useful in preparing chiral pheromones were thoroughly r e ~ i e w e d ~ GeneralMethods The present status of pheromone biochemistry was compiled as a monograph.4 Three general reviews on insect pheromones become Ritter reviewed steric factors in pheromonal pest control;8 he also reviewed his own applied research on semio~hemicals.~ A concise review on chiral insect pheromones was published in Czech I' Schneider reviewed the problem of insect olfaction I' A comprehensive review became available on structure determination of pheromones by combined microchemical and gas chromatographic methods The following additional reviews were published: a short reviewI3 an account of the background of pheromone research and its application in insect pest c o n t r o ~ 'I5 ~' a thorough review covering the literature published in 1982 and 198316 a review on isoprenoid pheromones (in Russian)I7 a pedagogical review on chirality in insect communication18 an account of the pheromone metabolism in insects" '* GENERAL METHODS Some useful methods for the synthesis and analysis of pheromones are listed below A Useful Synthetic Methods ( I ) Alkylation of Acetylides in DMSO In addition to the existing procedures for the alkylation of 1-alkynes,' Chong and Wong proposed a method employing methyllithium (base) and DMSO (solvent).*' As shown in Eq 1, terminal acetylenes afford disubstituted acetylenes in good yield (7747% yield) R=CH,OTHP, CH,OCH,Ph, Ph, CH(OEt), R=n-C,H,,, n-C,,H,, Me,CHCH, X-CI Br I References 519 1134 Pothier N.; Rowan, D D.; Deslongcharnps, P.; Saunders, J K Can J Chern 1981, 59, 1132 1135 Francke, W.; Hindorf, G.;Reith, W Nafurwissenschaferi 1979, 66, 619 1136 Deslongchamps, P.; Rowan, D D.; Pothier, N ; SauvC, T ; Saunders, J K Can J Cliern 1981, 59, 1105 1137 Byers, A.; Hogberg H.-E.; Unelius, C R.; Birgesson, G.;Lofqvist, J J Cheai Ecol 1989, 15, 685 (and refs therein) 1138 Francke, W ; Reith, W Liebigs Ann Cheni 1979, 1139 Phillips, C.; Jacobson, R.; Abraham, B.; Williams, H J.; Smith, L R J Org Cherri 1980, 45, 1920 1140 Jacobson, R.; Taylor, R J.; Williams, H J.; Smith, L R J Org Chetn 1982, 47, 3140 1141 Kozhich, A.; Segal, G.M.; Torgov, V Izu Akad NaukSSSR, Ser Khitrr 1982,325 1142 Ireland, R E.; Habich, D Terrahedrori Lett 1980, 21, 1389 1143 Ireland, R E.; Habich, D Chetn Ber 1981, 114, 1418 1144 Rosini, G.;Ballini, R.; Petrini, M.; Marotta, E Angew Chettr., Inr Ed Etigl 1986, 25, 941 1145 Zschiesche, R.; Hafner, T ; Reissig, H.-U Liebigs Anti Chenr 1988, 1169 1146 Doherty, A M.; Ley, S V.; Lygo, B.; Williams, D J J Chetn Soc., ferkiri Trans 1984, 1371 1147 Cekovic, Z.; Bosnjak, J Croat Chirn Acta 1985, 58, 671 1148 Koppenhofer, B.; Hinzer, K ; Weber, R.; Schurig, V Atigew Cliern Itit Ed Erigl 1980, 19, 47 1149 Redlich, H ; Francke, W Angew Chetn Itit Ed Erigl 1980, 19, 630 1150 Redlich, H Liebigs Ann C/ierri 1982, 708 1151 Hungerbuhler, E.; Naef, R.; Wasmuth, D.; Seebach, D.; Loosli, H.-R.; Wehrli, A Helv Chirn Acfa 1980, 63, 1960 1152 Enders, D.; Dahmen, W ; Dederichs, E.; Weuster, P Syrrrh Conirriurr 1983, 13, 1235 1153 Hogberg, H.-E.; Hedenstrom, E.; Isaksson, R.; Wassgren, A.-B Acta Chetti Scond 1987, 841, 694 Francke, W.; Reith, W.; Bergstrom, G.; Tengo, Natunuisserrschafretr 1980, 67, 149 Francke, W.; Reith, W.; Bergstrom, G ; Tengo, Z Naturforsch 1981, 36c, 928 Francke, W ; Hindorf, G.; Reith, W Arigew Cheni., h r Ed B i g l 1978, 17, 862 Ley, S V.; Lygo, B Tetrahedron Leu 1982, 23, 4625 1158 Rosini, G ; Ballini, R.; Maroha, E Tetrahedron 1989, 45, 5935 1159 Utimoto, K Pure Appl Chetn 1983, 55, 1845 1154 1155 1156 1157 1160 Hinzer, K.; Weber, R.; Schurig, V Tetrahedron Left 1981, 22, 55 1161 Ley, S V.; Lygo, B.; Wonnacott, A Tctrahedroti Let! 1985, 26, 535 1162 Ley, S V ; Lygo, B.; Sternfeld, F.; Wonnacott, A Telrahedroti 1986, 42, 4333 1163 Iwata, C ; Hattori, K.; Uchida, S.; Imanishi, T Tetrahedron Lett 1984, 25, 2995 Y.;Sugiyama, K.; Fujita, M ; Imanishi, T Tetrahedroti Lett 1987, 28, 2255 1165 Iwata, C.; Moritani, Y ; Sugiyarna, K.; Izaki, H.; Kuroki, T.; Irnanishi, T Cheni fliartri 1164 Iwata, C ; Moritani, Brill 1988, 36, 4785 1166 Francke, W personal communication dated February 25, 1990 520 1167 1168 1169 1170 1171 1172 1173 1174 1175 1176 1177 1178 1179 1180 1181 The Synthesis of Insect Pheromones, 1979-1989 Kotluk T.; Cottier, L.; Descotes, G Tetrahedron 1981, 37, 1875 Ley, S V.; Lygo B TefrahedroriLcrf 1984, 25, 113 Ley, S V.; Lygo, B.; Organ, H M.; Wonnacott, A Tetrahedron 1985, 41, 3825 Mori, K.: Sasaki, M.; Tamada, S ; Suguro, T.; Masuda, S Tetrahedron 1979,35, 1601 Francke, W.; Hindorf, G.;Reith, W Nufurwisserischafen 1979, 66, 618 Bergstrom ;Tengo, J.; Reith W.; Francke, W Z Naturforsch 1982, 37c, 1124 Mori, K.; Ikunaka, M Tefrahedron 1984, 40, 3471 Davies, N W.; Madden, J L J Chern Ecol 1985, 11 I 15 Kitching, W.; Lewis, J A.; Fletcher, M T.; Drew, R A I.; Moore, C I.; Francke, W J Chern Soc., Chem Cotnmun 1986, 853 Kitching, W.; Lewis, J A.; Perkins, M V.; Drew, R.; Moore, C J ; Schurig, V.; Konig, W A.; Francke, W J Org, Chetn 1989, 54, 3893 Mori, K.; Soga, H ; Ikunaka, M Liebigs Ann Chetn 1985, 2194 Baker, R.; Herbert, R.; Howse, P E.; Jones, T.; Francke, W.; Reith, W J Chern Soc., Chem Cornniuri 1980, 52 Baker, R.; Herbert, R H J Chem Soc., Perkin Traris 1987, 1123 Baker, R.; Herbert, R H.; Parton, A H J Chem Soc., Chem Cortiniun 1982, 601 Mazomenos, B E.; Haniotakis, G E J Chern Ecol 1985, I / , 397 1182 Brinker, U H.; Haghani, A.; Gomann, K Angew Chern Inf Ed D i g / 1985, 24, 230 1183 De Shong, P.; Waltermire, R E.; Ammon, H L J Ani~ Chem Soc 1988, 110, 1901 1184 Mortimore, M.; Kocieriski, P 7etrahedroti Len 1988, 29, 3357 1185 Brimble, M A.; Officer, D L.; Williams, G M Tetrahedron Lett 1988, 29, 3609 1186 Kociefiski, P.; Yeates, C Tetrahedroti Leu 1983, 24, 3905 1187 Kay, T.; Williams, E C Tetrahedron Lerr 1983, 24, 5915 1188 Redlich, H.; Francke, W Atigew Cherti., Itit Ed Erigl 1984, 23, 519 1189 Mori, K.; Uemalsu, T.; Watanabe, H.; Yanagi, K.; Minobe, M Tetrahedron Left.1984, 25, 3875 1190 Mori, K.; Uematsu, T.; Yanagi, K.; Minobe, M Terrahedrori 1985, 41, 27.51 1191 Mori, K.; Watanabe, H.; Yanagi, K.; Minobe, M Tetruhedrorr 1985, 41, 3663 1192 Iwata, C.; Fujita, M ; Hattori, K.; Uchida, S ; Imanishi, T Tefrahedroti Leu 1985, 26, 2221 1193 Iwata, C ; Fujita, M ; Kuroi, T.; Hattori, K.; Uchida, S.; Imanishi, T Chetn Pliant, Bull 1988,36, 3257 1194 Mori, K.; Watanabe, H Terrnhedrori Left 1984, 25, 6025 1195 Bestmann, H J ; Schmidt, M TefrahedroriLett 1986, 27, 1999 1196 Chen, J Y C ; Hough, L.; Richardson, A C J Cherti Soc., Chetti Cotttrtiutt 1982, 1152 1197 Chen, J Y.C : Hough, L.: Richardson, A C J Cherti Soc., Perkhi Traris 1985, 1457 1198 Haniotakis, G.; Mavraganis, V G.;Ragoussis, V J Cheni Ecol 1989, 15, 1057 1199 Haniotakis, G ; Francke, W.; Mori, K.; Redlich, H ; Schurig, V J Chetti Ecol 1986, 12, 1559 1200 Tengo, J ; Agren, L.; Baur, B.; Isaksson, R.; Liljefors, T.; Mori, K.; Konig, W.; Francke, W J Chem Ecol 1990, 16, 429 References 521 1201 Kitching, W.; Lewis, J A.; Fletcher, M T ; De Voss, J J ; Drew, R A 1.; Moore, C J J Chem Soc., Chetn Cornmun 1986, 855 1202 Mori, K.; Tanida, K Heferocycles 1981, 15, 1171 1203 Mori, K.; Tanida, K Terrahedron 1981, 37, 3221 1204 Mori, K ; Watanabe, H Terrahedron 1986, 42, 295 1205 Isaksson, R.; Liljefors, T ; Reinholdsson, P J Chetn Soc., Cherti Cornrnun 1984, 137 1206 Redlich, H.; Schneider, B Liebigs Ann, Cherti 1983, 412 1207 Redlich, H ; Schneider, B.; Hoffmann, R W.; Geueke, K.-J Liebigs Ann Cheni 1983, 393 1208 Mori, K ; Katsurada, M Liebigs Ann Chenf 1984, 157 1209 Bell, T W ; Bopprk, M.; Schneider, D ; Meinwald, J Experienfia 1984, 40, 713 1210 Bopprk, M ; Schneider, D.J Cotnp Physiol A 1985, 157, 569 1211 Roder, E.; Wiedenfeld, H ; Bourauel, T Liebigs Ann Chetti 1986, 1645 1212 Krasnoff, S B.; Dussourd, D E J Chern Ecol 1989, 15, 47 1213 Talman, E.; Ritter, F J.; Verwiel, P E J ; In Mass Specrroinerry in Biocliernisrry arid Medicine; Frigerio, A., and Castagnoli, N Eds Raven Press: New York, 1974, 197-217 1214 Royer, J.; Husson, H.-P J Org Chew 1985, 50, 670 1215 Macdonald, T L J Org Chetn 1980, 45, 193 1216 Stevens, R V ; Lee, A W M J Chenr SOC Chem Cornmcn 1982, 102 1217 Iida, H ; Watanabe, Y.; Kibayashi, C Terrahedron Lett 1986, 27, 5513 1218 Watanabe, Y.; lida, H.; Kibayashi, C J Org Chem 1989, 54, 4088 1219 Yamaguchi, R.; Hata, E.; Matsuki, T ; Kawanishi, M J Org Chern 1987, 52, 2094 1220 Jefford, C W.; Tang, Qian, Zaslona, A Helv Chirn Acra 1989, 72, 1749 1221 Yamazaki, N ; Kibayashi, C Terrahedrori Lerr 1988, 29, 5767 1222 Chuman, T.; Landolt P J.; Heath, R R.; Tumlinson, J H J C h r i Ecol 1987, 13, 1979 1223 Attygale, A B.; Morgan, E D J Chetn Ecol 1984, 10, 1453 1224 Masaki, Y.; Iwata, I.; Imaeda, T.; Oda, H ; Nagashima, H In Absfracrs of Papers, 16th Infernarional Sytnposiutn on the Chemisfry of Narural Producrs (IUPAC) Kyoto, Japan, 1988, PB 102 (p 348) 1225 Hurter, J.; Boller, E F.; Stadler, E.; Blattmann, B.; Buser, H.-R.; Bosshard, M U ; Damm, L.; Kozlowski, M W.; Schoni, R ; Raschdorf, F.; Dahinden, R.; Schlumpf, E.; Fritz, H ; Richter, W J ; Schreiber, J Experienria 1987, 43, 157 1226 Ernst, B.; Wagner, B Helv Chirn Acra 1989, 72, 165 1227 Kametani T ; Tsubuki, M ; Honda, T Chetn Plrurm Bull 1988, 36, 3706 1228 Kametani, T ; Tsubuki, M.; Tatsuzaki, Y ; Honda, T J Clietn S o c , Perkin Trans 1990, 639 1229 Kuwahara, S.;Mori, K Tetrahedron 1990, 46, 8083 The Total Synthesis of Natural Products, Volume9 Edited by John ApSlmon Copyright © 1992 by John Wiley & Sons, Inc Subject Index Acanfhoscelides obfectus, 12 Acarid mite, 116 3-Acetoxy-2,6-dimethyl- ,5-heptadiene,(R), 286 6-Acetoxy-5-hexadecanolide,(5R,6S), 252 3-Acetoxy-7-methyl-6-nonene,(3R, 6E), 285 Achroia grisella, 138 Adoxophyesfascia fa, 36 Adoxophyes orana, 36 Adoxophyses species, I19 African monarch butterfly, 318, 478 African sugarcane borer, 348 Agroniyra frontella, Agrotis segerurn, 25 Alfalfa blotch leafminer, Allofarnesene,(Z, Z, Z ) , 276 Almond moth, 69 Alsophila potnetaria, 79, Alsophila quadripuncfafa, 80 Arnathes c-nigruni, 34 Ambrosia beetle, 280 American cockroach, 336, 341, 343 Amyelois transitella, 134 Anasfrepha ludens, 360 Anasrrepha suspensa, 360, 362 Anastrephin, 360 Andreno haemorrhoa 449, 459, 461, 477 Andrena wilkella, 449, 471, 476 Anobium punctatutn, 377 Anorriala rufocuprea, 10 Ant, 101 Ant lion(s), I I I , 374 Aiitheraea polyphenius, 70 Anthonoinus grandis, 303, 17, 334 Anfhrerius verbasci, 10 Anticarsia geniniatalis, 82 Aonidiella auranti, 320 Aoriidiella cifrina, 326 Aphis gossypii, 274 Aphornia gularis, 226 Apple clearwing moth, 78 Apple leafminer moth, 36 Archips seniifcranus, 24, 37 Arctiid moth, 66, 83, 478 Arcfiidae, 66 Argentine ant, 132 Asian corn borer moth, 24 Atlagenus elongatulus, 12 Attagenus niegafonia, I Atta texana, I77 Australian fruit fly, 473 Azuki bean weevil, 345 Bagworm moth, 101 Banded cucumber beetle, 185 Bark beetle, 303 370, 371 Bishomomanicone, 179 Black carpet beetle, 21 I Blattella germanica, 185 Boarniia selenaria, 79 Boll weevil, 317, 334 Bombykol [ 10,12-hexadecadien-l-oI], (IOE,12Z), 59 Bornbyx inori, 59 523 524 Subject Index Bontebook, 157 Brachrnia ntacroscopa, 25 Bredius maridibularis, 234 endo-Brevicomin,( IR,5S,7S), 394 exo-Brevicomin,( IR,5S,7R), 394 2-sec-Butyl-4,5-dihydrothiazole, 482 2-Butyl-8-methyl- 1,7dioxaspiro[5.5]undecane, 475 Cabbage looper, 26 Cabbage moth, 25, 37 Cabbage webworm, 134 California five-spined ips, 294 California red scale, 320 Callosobruclnts chinensis, 345 Callosobruchusic acid, 345 Cartipotlotus herculeanus, 232 Canipoiiotus rtoveboracerisis, 232 Canipotiotus penrrsylvarricits 232 Canadian red-sided garter snake, 175 Caribbean fruit fly, 360, 362 Carob moth, 132 Carpenter ants, 232 Carpenter bee, 220 Carpenter worm moth, 55 Carpo.ria niporlensis, I58 Cathartus quadricollis, 285 Cedra caurello, 69 Ceratiris capitata, 18 Cereal tortix moth, 23 Chalcogran, 209, 446 Chenytree borer, 78 Chilo srtppressalis, 133, 139 Cigarette beetle, 193, 379 Cisseps fulvicollis, 478 Citrus flower moth, 131 Citrus mealy bug, 312 Cleunving moth, 74 Ctrephasia punricatra, 23 Cocoa pod borer, 84 Codling moth, 48 Common furniture beetle, 377 Common wasp, 45 , 455 Comstock mealybug, 286 Confused flour beetle, 141 Conophthorus sp., 455 Conopotirorpha cramerella, 84 Corcyra cephalonica, 330, 336 Cossus cossus, 69 Cotton aphid, 274 Cotton boll weevil, 303 Cotton boll worm, 133 Cotton leafworm, 56 Creatonotos gangis, 79, 95, 478 Creatonotos transiens, 79, 95, 478 Cremamgasrer, 178 Creniatogaster castanea, 108 Crernarogaster lienqniei, 108 Cryptolesfesferrugineus, 265, 364 Crypiolestes piisillus, 265, 270 Cryptolestes turcicus, 270, 27 I Cryptophlevia leucoreta, 20 Cucumber fly, 459, 471 Culex pipieris fatigaris, 252 Culex tarsalis, 264 Cylas fortnicarius elegantirlits, 20 Dacus cacitttiiiiatits, 470 Dacits cuctimis, 459, 471 Dacus cucurbitae, 18, 233 Dacus dorsalis, 473 Dacus halfordiae, 193, 471 Dacits latijirons, 473, 475 Dacus occipitalis, 193, 473 Dacus oleae, 462 Darrialiscus dorcas dorcas, 157 Danaidal, 478 Danaidone, 478 Dariaus chrysippus, 318, 478 Danaus gilippus berenice, 478, 320 Danaus plexipptis, 346, 347, 380 2,4,6-Decalrien-5-olide,(2Z,4Z,6E), 230 5-Decenyl acetate.(Z), 28 5-Decenyl isovalerate,(Z), 160 Dendroctorius bretdcomis, 38 I , 394 Dendroctonus frontalis, 38 I , 394 Dendroctonus pseudotsugae 15, 16, 38 I Detidrolittius punctafus, 38 Dendrolitnus speciabillis 38, 41 Deodar weevil, 333 Dermestid beetles, 152, 216 Diabrotica balteata, 185 Diabrotica barberi, I13 Diabrotica lotigicornis, I 13 Diabrotica porracea, I13 Diabrotica undeciinpunctata horvardi I8 I Diabroiica virgifera virgifera, 13 Diabrotica virgifera zeae, I13 Diamond black moth, 37 Dichocrocis puiicriferalis, 133 Subject Index 525 7, 1-Dimethyl-3-methylene-1,6,10dodecatriene,(E), 274 3, I-Dimethyl-2-nonacosanone,(3S, IS), 185 2,3-Dihydro-3,5-dimelhyl-2-ethyl-6-( I 'methyI-2'-hydroxoybutyI)-4H-pyran-one, 3, -Dimethylnonadecane,9 379,380 I ,7-Dimethylnonylpropanoate, 113 2,3-Dihydro-2-isopropyl-2,5-dimethylfuran, 3,7-Dimethyl-2,6-octadienyl formate,(Z), 29I 3,7-Dimethyl-2,7-octadienylpropanoate,(E), 371 291 2,3-Dihydro-7-1nethylI H-pyrrolizin-1-one, 3,7-Dimethyl-2,7-octadienyl propanoate,(Z), 478 291 2,3-Dihydro-2,3,5-trimethyl-6-( I '-1nethyl-23.7-Dimethyl-2-octeneI ,I-dioicacid,@), 345 oxobutyl)-4H-pyran-4-one, 374 ,8-diol,(E), 18 2,3-Dihydro-2,3,5-trimethyl-6-(2'-hydroxy-l-3.7-Dimethyl-2-octene-l 3,7-Dimethyl-6-octen-4-olide,(3S,4R), 348 methylbutyl)-4H-pyran-4-one,378 4,6-Dimethyl-4-octen-3-one,(4E,6S), 179 3,3-Dimethyl-A'~P-cyclohexaneethanol,(E), 6,12-Dimethyl-2-pentadecanone,(6R, 12R), 334 I ,7-Diethyl1,6-dioxaspiro[4.4]nonane,449 Dihydroactinidiolide,(R), 356 3,3-Dimethyl-A',P-cyclohexaneethanoI,(Z), 317 4,8-Dimethyl-3,8-decadienIO-olide,(3E,IE), 362 4,8-Dimethyl-4,8-decadienIO-olide,(4E,8E), 364 3,7-Dimethyl-2,6-decadieneI , l0,dioic acid,(2E,6E), 347 3,7-Dimethyl-2,6-decadiene-l, 10dio1,(2E,6E), 320 4,8-Dimethyldecanal(triborlure),(4R,8A),141 I ,3-Dimethyl-2,9-dioxabicyclo[3.3 I)nonane, 435 I ,5-Dimethyl-6,8-dioxabicyclo[3.2 lloctane, 381 1,6-dioxaspiro[4.6]undecane, 2,7-Dirnethyl461 2,8-DirnethylI ,7-dioxaspiro[5.5]undecane, (2S,6R,8S),470 2.8-Dimethyl-I ,7-dioxaspiro[5,5]undecane-401, 476 1,8-Dimethyl-3-ethyl-2,9- dioxabicyclo[3.3.I]non-7-ene,(IR,3S,5S), 435 I ,S-Dimethyl-3-ethyl-2,9- dioxabicyclo[3.3.l]non-7-en-6one,(lR,3S,SR), 435 2,4-Dimethyl-5-ethyI-6,8dioxabicyclol3.2.Iloctane,428 5,9-Dimethylheptadecane,5S, 9.9, 3,6-DimethyI-2,4-heptanedione, 176 2,6-DimethyI-5-heptenal, 157 17,21-Dirnethylhep1atriacontane-~neso,13 3,5-Dimethyl-6-( I '-methylbuty1)-tetrahydro2H-pyran-2-one,(3R,SR,6S, I 'R),227 185 15,23-Dirnethylpentatriacontane-meso,12 15,19-Dimethyltritriacontane, 10 I ,7-Dioxaspiro[S.51undecane,462 Diparopsis castanea, 23, 50 Diprion sirnilis, 128 I ,7-Dipropyl1,6-dioxaspiro[4.4]nonane,449 Disparlure, 85 3,6-Dodecadien-l l-olide,(32,6Z,I IR), 268 3,6-Dodecadien12-olide,(3Z,6Z), 267 5,7-Dodecadienal,(SE,72),I31 5,7-Dodecadienl-o1,(5Z,7E), 38 5,7-DodecadienI-o1,(5Z,7Z), 4I 8,IO-Dodecadien-1-01,( E ,1O E ), 48 8.IO-Dodecadien-I-o1,(8Z, IOE), 49 7-9-Dodecadienylacetate,(7E,9Z), 42 9,lI-Dodecadienylacetate,@), 50 9,lI-Dodecadienylacetate,($), 54 4-Dodecanolide,234 3,6,8-Dodecatrien-I-o1,(3Z,6Z,8E) 84 3-Dodecen-ll-olide,(3Z,IIS),265 3-Dodecen-12-olide,(Z),265 7-Dodecenyl acetate,(E)-, 20 7-Dodecenyl acetate,(Z)-, 29 8-Dodecenylacetate,@)-, I 8-Dodecenyl acetate,(Z)-, I 9-Dodecenylacetate,@)-, 23 9-Dodeceny l acetate,(Z)-, 32 3-Dodecenyl(E)-2-butenoate,(Z),201 Dominicalure I , 99 Dominicalure , 99 Douglas fir beetle, 315,316,381 Douglas fir tussock moth, 165 Dried bean beetle,212 Drosophila busckii, 130 526 Subject Index Drosophila malerkotliana, 37 Drosophila inelanogasfer, 66 Drosophila tnulleri, 122, 158 Drugstore beetle, 374, 378 Dryocetes confusus, 394 Dryocetes autographus, 394 Earias insulana, 133 Earias vittella, 138 Eastem subterranean termite, 84 Eastem spruce budworm, 132 Ectotnyelois ceratoniae, 132 Eight-toothed engraver beetle, 296 Egyptian cotton leafworm, 56, 139 Eldatra saccharina, 348 Elm bark beetle, 370 Engelmann spruce weevil, 332 Epianastrephin, 360 Epiphyas posfwittana, 56 9, IO-Epoxy-3,6henicosadiene,(32,62,9S,10R), 95 9.10-Ep0~y-l,3,6henicosatriene,(3Z,6Z,9S,IOR), 98 9,10-Epoxy-6-henicosene,(6Z,9S, IOR), 94 IOR), 9,lO-Epoxy-1,3,6-icosatriene,(32,6Z,9S, 98 2-(3’,4’-Epoxy-4’-methylcyclohexy)-6methylhepta-2,5- diene,(l’S,3’R,4’S,Z),(3’S,4’R), 33 I 7,8-Epoxy-2-methyloctadecane,(7R,8S), 85 9,IO-Epoxytetrahydroedulan, (1R,2S,4S,7R,IOS),380 En silkworm, 138 2-Ethyl-8-methyl-1,7dioxaspiro[5.Slundecane, 473 I-Ethylpropyl (2S,3R)-2-methyl-3hydroxypentanoate, 203 Euploea boisdrrvalii, 380 Euploea eusipires, 280 Euploea klugii, 380 Euploea leucosfioos, 380 Euploea mulciber, 380 Euploea fulliolus, 380 Eupoecilia (Clysia) atnbigitella, 32 Euroleorr nostras Crocus bore, I I European cherry fruit fly, 484 European goat moth, 69 European grape beny moth, I European pine sawfly, 128 European pine shoot moth, 23 Fall armyworm, 36 Fall cankerworm moth, 79, 81 Fall webworm moth, 98 False codling moth, 20 Faranal, 148 Farnesal,(E,E), 336 Farnesal, (Z,E), 336 a-Famesene,(E,E), 273 a-Femesene,(Z,E), 273 @-Farnesene,(E),274 Fermlacetone 11, 265 Ferrulactone I, 364 Flat grain beetle, 265, 270 Forest tent caterpillar, 38 Fortnicu polycletra, 202 Formica rufa, 202 Esfigtnene acrea, 95 2-Ethyl-I ,6-dioxaspiro[4.4]nonane,446 l-Formyl-6,7-dihydro-5H-pyrrolizine, 478 1-Formyl-6,7-dihydro-5H-pyrrolizin-7-ol, 478 one,(R), 367 2-Ethyl-6-methyl-2,3-dihydro-4H-pyran-4one,@), 367 errdo-7-Ethyl-5-methyl-6,8dioxabicyclo[3.2.lloctane, 394 exo-7-Ethyl-5-methyl-6.8dioxabicyclo[3.2.Iloctane, 394 exo-7-Ethyl-5-methyl-6.8diaxabicyclo[3.2.I]oct-3-ene, 424 2-Ethyl-7-methyl-1,6-dioxaspiro[4.5]decane, 459 7-Ethyl-2-methyl-1,6-dioxaspiro[4.5]decane, 459 Fruit fly, 67, 193 2-Ethyl-2-methyl-2.3-dihydro-4H-pyran-4- Frontalin,(lS,SR), 381 Geometrid moth(s), 66, 80 Geornetriidae, 66 Geman cockroach, 185 Giant looper, 79 Glossina rnorsitans morsfians, I3 Glossina pallidipes, 12, I3 Goasyplure, 71 ( l5R)-2-{[ I ~-9-D-G~ucopyranosy~)oxy]-8hydroxyhexadecanoy llamino }ethanesulfonic acid, 484 Glyphodes pyloalis, 84 Subject Index Gnathatrichus sulcatus, 280 Goumois grain moth, 73 Grain beetle, 270, 271 Granary weevil, 203 Grandisal, 332 Grandisol, 303 Grape borer, 109, 191 Grape berry moth, 33 Grape root borer, 74 Grape vine moth, 42 Grapholiia niolesta, I Grapholitha molesta, I Green bug, 364 Green stink bug, 33 I Grocus bore, 374 Gypsy moth, 85 Heart and dart moth, 33, 36 Hedya ochroleucana, 49 Helioihis antrigera, 133 Helioihis virescens, 133 Hellula utidalis, 134 3,6-Henicosadiene,(32,62), 66 6,9-Henicosadiene,(6Z,9Z), 66 1,6-Henicosadien-l I-one,(Z), 165 I ,3,6,9-Henicosatetraene,(3Z,6Z.92), 83 3.6,9-Henicosatriene,(3Z,62,9Z), 82 6-Henicosen-1 I-one,(Z), 165 Hepialone, 367 Hepialus californicus, 367 Hepialus hecia, 368, 435 , l I-Heptacosadiene,(7Z, IZ), 67 IO-Heptadecen-2-one,(Z),158 I I-Hexadecen- 13-ynyl-acetate,(Z), 63 13-Hexadecen-l I-ynyl-acetate,(Z), 61 I I-Hexadecenyl acetate, ( E ) , 25 I-Hexadecenyl acetate, (Z), 37 11,13-Hexadecadienyl acetate,(l IZ, 13E), 63 4-Hexanolide, 216 Holomelina aurantiaca, Homofarnesene,(E,E), 277 Homo farnesene, (Z,E), 277 Homomanicone, 179 10-Homonerol oxide, 374 Honeybee, 203, 204 House fly, 25 House mouse, 425, 482 Hydroxydanaidal, 478 9-Hydroxy-2-decenoic acid,@), 203 IO-Hydroxy-3,7-dimethy1-2,6-decadienoic acid,(2E,6E), 346 29-Hydroxyl-3,l I-dimethyl-2nonacosanone,(3S,l IS), 185 7-Hydroxy-4,6-dimethyl-3-nonanone, (4S,6S,6S), 193 3-Hydroxy- 1,7-dioxaspiro[5 Slundecane, 462 4-Hydroxy- 1,7-dioxaspiro[5 S]undecane, 462 1-Hydroxy- 1-methylethyI)-5methyltetrahydrofuran,cis,370 I -Hydroxy- I -methylethyl)-5methyltetrahydrofuran,trans, 370 5-Hydroxy-4-methyl-3-heptanone,(4S,5R), I89 2-Hydroxy-3-octanone,(S),191 Hylecoetrrs dermesioides, 37 I Hyphaniria cunea, 95, 98 5-(3E,6-Heptadienyl)-dihydro-2(3H)-furanone, 3,6,9-Icosatrien,(3Z,6Z,9Z), 82 233 5-Hexadecanolide,(R), 242 10,12-Hexadecadienal,(IOE~ 12E) 133 I1,13-Hexadecadienal,( IIE,13E), 134 I1,13-Hexadecadienal,(I 1Z,132), 134 6,1 I-Hexadecadienyl acetate,(6E, I IZ), 70 7, I I-Hexadecadienyl acetate,(7Z, I Z ) , 71 7,11-Hexadecadienyl acetate,(7Z,I I E ) , 71 I IZ), 138 4,6,1 I-Hexadecatrienal,(4E,6E, 4,6,lO-Hexadecatrienyl acetate,(4E,6E, IOZ), 84 4.6.10-Hexadecatrienyl acetate,(4E,62, IOZ), 84 7-Hexadecenal,(Z), 132 I-Hexadecenal,(Z), 133 527 13-Icosen- IO-one,(Z), 158 I-Icosenyl acetate,(Z), 37 Indian meal moth, 69 Introduced pine sawfly, 128 Invictolide, 227 Ipsdienol, 294 Ipsenol, 294 Ips paracot?firsus, 294 Ips pirii, 295 Ips typographus, 296 Iridomynnex huriiilis, I32 Iris borer, 133 Isopenplanone-A, 341 3-lsopropenyl-2,2-dimethylcyclobutanemethyl acetate,(lR,3R), 312 528 Subject Index 1-1sopropenyl- 1-methycyclobutaneethanal,cis-, 303 332 Japanese beetle, 238 Khapra beetle, 152, 216 Lardoglyphus konoi, 116 Lardolure, I16 Lasioderma serricorne, 193, 379 Laspeyresia pomonella, 48 Leaf-cutting ant, 177 Leopard moth, 74 Lepfogenys diminufa, 101 Lesser grain borer, 99 Lesser peachtree borer, 75 Ducatiia separata, I33 Leucopiera sciiella, Light-brown apple moth, 56 Lineatin,( IR,4S.W,7R), 436 Lobesia boirana, 42 Lymaniria dispar, 85 Lyonefia clerkella, 15 Macronocrua onusfa, 133 Maize weevil 189 Malacosoma dissrria, 38 Male monarchy butterfly, 347 Mattiestra brassicae, 25 Manica bradleyi, 179 Manica tnutica, 176, I79 Manicu rubida, 179 Manicone, ( S ) , 179 Mafsucossus tnafsumurae, 184 Mafsucoccus resinosae, 184 Mafsucocciis fhunbergianae, 184 Matsuone, 184 Mediterranean fruit fly, 18 Megarhyssa norioni nortoni, 459, 471 Megaselia halferafa, 177 Megatomoic acid, I Megoltra viciae, 364 Melacosoma californicum, 13 Meliffia satyriniformis, 74 Melon fly, 18, 233 I-Methylbutyl decanoate,(R), 101 I-MethyIbutyl(E)-2,4-dimethyl-2pentenoate,(S), 99 I-Methylbutyl(E)-2-methyl-2-pentenoate,(S), 99 5-Methyl-3-butyloctahydroindolizine, 478 I-Methyl-2-cyclohexen- 1-01, 16 3-Methyl-2-cyclohexen-1-01 15 Methyl (2E,42)-2,4-decadienoate, 209 2-Methyl- 1,6-dioxaspir0[4.5]decane,45 7-Methyl-I ,6-dioxaspiro[4.5]decane,455 2-Methyl- 1,7-dioxaspiro[5.6]dodecane,477 1-Methyldodecyl acetate,@), 122 10-Methyldodecyl acetate, I19 4-Methyl-3-heptanol,(3S,4S), 101 2-Methylheptadecane, 4-Methyl-3-heptanone,(S),177 6-Methyl-5-hepten-2-01, 280 14-Methyl-8-hexadecena1, 152 4-Methyl-3-hexanol,(3R,4S), 101 2-Methyl-5-hexanolide,cis, 220 4-Methyl-3-hexanone,(S),176 3-Methyl-6-isopropenyl-3,9-decadienyl acetate,(R,Z), 320 3-Methyl-6-isopropenyl-9-decenyl acetate,(3S,6R), 320 3,9-Dimethyl-6-isopropenyl-3,9-decadienyl proponoate,(R,Z), 330 3,9-Dimethyl-6-isopropyl-5,8-decadienyl acetate,(S,E), 326 Methyl 3-isopropylpentanoate, 202 2-Methyl-6-methylene-2,7-octadien-4-ol, 294 2-Methyl-6-methylene-7-octen-4-ol, 294 7-Methyl-3-methylene-7-octenyl proponoate,(Z), 291 4-Methyl-l-nonanol,(R), I I I 14-Methyl-I-octadecene-(b),15 6-Methyl-3-octanone, 178 I2 Methyl (R,E)-2,4,5-tetradecatrienoate, Methyl (Z)-5-tetradecenoate, 10 I-Methyltetradecyl acetate.(S), 130 IO-Methyl-2-tridecanone,(R), 181 15-Methyltritricontane, 10 2-Methyl-6-vinylpyrazine, 482 Muscalure, 9-tricosene,(Z), 25 Mexican corn rootworm, 113 Mexican fruit fly, 360 Mocis laripes, 82 Mold mite, 291 Momesrra brassicae, 37 Monarch butterfly, 346, 380 Monomorine 1,(3R,5S,9S), 478 Monomorium pharaonis, 148, 478 Mountain-ash bentwing, Subject Index Mulberry pyralid, 84 a-Multistnatin,( IS,2R,4S,5R), 428 &Muhistriatin, 431, 433 Mushroom fly, 177 Mus musculus, 425, 482 Musca dornestica 25 Myrmica ants, 108 Myrtnica rubra, 108 Myrrnica scabrinodis, 108 Nasutiternies exitosrts, 277 Nasutiternres graveolus, 277 Nasutitermes rvalkeri, 277 Naval orangeworm, 134 Neocembrene,(E,E,E), 277 Neodipriorr lecotrtei, f28 Neodiprion pinetum, I28 Neodiprion sertifer, 128 Nepetalactol,(lR,4aS,7S,7aR),364 Nepetalactone,(4aS,7S,7aR), 364 Neryl formate, 291 New Zealand leafroller moth, 34 Nezara viridula, 33 I 7,l l-Nonacosadiene,(7Z,IIZ), 67 6,9-Nonadecadien-3-one,(6Z,9Z), 165 3,6-Nonadecadiene,(32,62),66 3,6,9-Nonadecatnene,(32,6Z,9Z), 79 I ,3,6,9-Nonadecatetraene,(3Z,6Z,92), 81 3,6,9,1l-Nonadecatetraene,(32,62,92,I I E ) , 81 3,6,9, I l-Nonadecatetraene.(32,6Z,92,1IZ), 81 12-Nonadecen-9-one,(Z),158 2,6-Nonadien-4-oIide,(22,6Z), 226 6-Nonen-l-ol,(E), 18 6-Nonenyl acetate,(E), 18 Normanicone, 179 Northern corn rootworm, I13 Northern pine weevil, 332 Nostrenol,(R), 11 Nudaurelia cytherea cytherea, 160 Oak leafroller moth, 24, 37 Oak processionary moth, 63 2-Ochtoden-l-al,(E), 334 2-Ochtoden-1-al,(Z), 334 2-Ochtoden-l-ol,(Z), 17 3,13-Octadecadien-l-ol,(3E, 13Z), 76 2.13-Octadecadienyl acetate,(2E, 132) 74 3,13-Octadecadienyl acetate,(3E, 13Z), 76 3,13-Octadecadienyl acetate,(3Z,132) 74 529 I-Octadecenal,(Z), 138 13-Octadecenal,(Z), I39 2,3-0ctanedio1,(2S,3S), 109 3-Octano1, 108 Olive fruit fly, 462 Omniferous leafroller moth, 24 Qperophrhera brunrata, Qrgyia pseudotsugata, I65 Oriental hornet, 242 Oriental fruit fly, 473 Oriental fruit moth, 21, 26 Qryzaephillus nrercutor, 265, 268 OrymephiNus surinamensis, 267, 268, 27 I Ostrina ficrnacalis, 24 9-0x0-2-decenoic acid,@), 204 2-0~0-4-ethenyI-4,7a-dimethyl-2,4,5,6,6,7a- hexahydrobenzofuran, 360 6-Oxo-l-nonanol, 193 2-0~0-4,4,7a-trimethyl-2,4,5,6,6,7ahexahydrobenzofuran,(R), 356 Pharaoh’s ant, 148,478 Palaearctic bee, 449 Papaya fruit fly, 482 Paralobesia viteana 33 Paranthrene tabaniforinis, 76 Parasitoid wasp, 459, 47 I Paravespula vulgaris, 45 455, 459 Peach fruit moth, 158 Peach miner moth, 15 Peach tree borer, 75 Pectinophora gossypiella, I 7,1 I-Pentacosadiene,(7Z, I IZ), 67 230 I-Pentenyl)-2H-pyran-2-one),(E), Peribatodes rhomboidaria, 165 Penplanone-A,(-), 341 Penplanone-B,( -), 336 Penplanone-C, 343 Periplanone-D, 343 Periplaneta americana, 336, 341, 343 Phragrnatobia fuliginosa, 94 Phthoritriaea opercufelfa,68 Phyllonorycter ringotriella, 36 Pine bast scales 184 Pine emperor moth, 160 Pine engraver, 295 Pine moth, 38, 41 Pink bollworm moth, 71 Pissodes approximatus, 332 Pissodes netnorensis, 333 Pissodes strobi, 332 530 Subject Index Pifyogenes chalcographus, 209, 446 Pityol,cis, 370 Pityol,(2R,SS)-frans, 370 Pityophthorus pityographus, 303, 370 Ptanococcus cirri, I2 Planotortrix excessana, 34 Platynora srultana, 24 Plirfella xylostella, 37, 133 Popilliu japoriicu, 238 Poplar twig clearwing moth, 76 Potato tubenvorm moth, 68 Prays cifri, I3 I Prinoxystus robiniae, 55 Processionary moth, 63, 64 Pseudaulucaspic pentagona, 330 Pseudococcirs comstocki, 286 Pfeleobirts viffatus,370, 37 I Purple stem borer, 37 Pyralid moth, 226 Quadruspirliotiisperniciosirs, 29 I Quadrilure, 285 Queen butterfly, 320, 478 Red bollworm moth, 21, 50 Red flour beetle, 141 Red-headed pine sawfly, 128 Red iniported fire ant, 227, 273, 276, 277, 356 Red wood ant, 202 Reficulirerniesjavipes, 84 Reficuliternies virginicus, 84 Rhagolefis cerasi, 484 Rhyucionia buoliana, 23 Rhyzopertha doniiirica, 99 Rice moth, 330, 336 Rice stem borer, 133, 139 Rice weevil, 189 Rove beetle, 234 Ruby tiger moth, 94 Rusty grain beetle, 265, 364 Salt marsh caterpillar moth, 95 Sarnia Cynthia ricini, 138 San Jose scale, 291 Sawtoothed grain beetle, 267 Sceliodes cordalis, 25 Schizaphis grantinurn, 364 Scolytus inulfistriatrrs, 101, 428 Scoria exclamafionis, 33, 36 Scrobipalpa heliopa, 23 Semcolone.(2S,3R, ' R ) , 379 Serricornin, 193 Serricorole,(2S,3R, 'S,2'S), 380 Sesatnia irferens, 37 Seudenol, 315 Silkworm moth, 59 Sitophilate, 203 Sitophilure, 189 Sifophilrts granarius, 203 Sifophilus orytae, 189 Sifophilus zeamais, I89 Sifotroga cerealella, 73 Six-spinned spruce bark beetle, 209, 446 Smaller cleanving moth, 74 Smaller European elm bark beetle, 101, 428 Small forest ant, 202 Smaller tea trotrix moth, 36, 119 Solenopsis invicfa, 227, 230, 273, 276, 277, 356 Southern armyworm moth, 69 Southern corn rootworm, 181 Southern house mosquito, 252 Southern pine beetle, 394, 381 Soybean beetle, 210 Spiny bollworm, 133 Spodopfera eridiana 69 Spodoptera frrigiperda, 36 Spodoptera littoralis, 56, I38 Spodoptera litura, 56 Spotted bollworm, 138 Spotted cutworm moth, 34 Spruce bark beetle, 296 Square-necked grain beetle, 285 Squash vine borer, Stable fly, 10 Stegobinone,(2S,3R, I'R), 374 Stegobiol,(2S,3R, I 'S,2'S), 378 Sfegobiurnpaniceurn, 374, 378 Stink bugs, 128 Sfirefrusanchorago, 128 Sfomrys calcitrans, 10 Striped ambrosia beetle, 435, 436 Subterranean termite, 84 Sulcatol, 280 Summerfruit tortrix moth, 36 Suspensolide, 362 Sweet potato leaf folder moth, 25 Sweet potato weevil, 201 Subject Index Swift moth, 368, 435 Synarirhedon acerrubri, 74 Synanrhedon exitiosa 75 Synanrhedon hecror, 78 Synanrhedon myopaefortnis, 78 Synanrhedon pictipes, 75 Synanrhedon renuis, 74 Tenebrio molitor, I I Termite, 277 9, I I-Tetradecadienal,(9Z,1 I E ) , 132 3,5-Tetradecadienoic acid,(3E,5Z), 21 I 33-Tetradecadienoic acid,(3Z,5Z), 12 5,s-Tetradecadien- I3-olide,(5Z,SZ, 13R), 27 3,5-Tetradecadienyl acetate,(3Z,5E), 55 , 13-Tetradecadieny l acetate,(Z), 69 9, I I-Tetradecadienyl acetate,(9E, I I E ) , 56 9,l I-Tetradecadienyl acetate,(92,1 IE), 56 9,12-Tetradecadienyl acetate,(92,12E), 69 9,11,13-Tetradecatrienal,(9Z,II E ) , 132 7-Tetradecenal,(Z), 13 I 9-Tetradecenal,(Z), 132 I-Tetradecenal,(E), 132 I-Tetradecenal,(Z), 132 5-Tetradecen-4-olide.(R.Z),238 5-Tetradecen- 13-olide,(5Z,13s) 269 5-Tetradecenyl acetate,(Z), 33 7-Tetradecenyl acetate,(Z), 34 9-Tetradecenyl acetate,(Z), 36 10-Tetradecenyl acetate,(Z), 36 I-Tetradecenyl acetate,(E), 24 I-Tetradecenyl acetate,(Z), 37 12-Tefradecenyl acetate,@), 24 Tetrahydro-2,2,6-trimethyl-2H-pyran-3ol,(3R,6S)-cis, 371 I ,3,5,7-Tetramethyldecyl formate,(lR,3R,5R,7R), I16 1,6,6,IO-Tetramethyl-3,11dioxatricyclo[5.4.0.02~4]undecane, 380 3,4,7,1 I-Tetramethyl-I,3,6,lOdodecatetraene,(3Z,6E,3E),277 Thaurnetopoea pityocattipa, 64 Thyridopteryx epherneraefortnis, 10I Tiger moth(s), 8, 66 Tobacco budworm, 133 Tobacco stem borer, 23 Toxorrypana curvicauda, 482 Triboliuni castaneutn, 141 Triboliutn cotifisutn, 14 Triboliumfreetnani, 14 I Trichoplusia n i , 26 4,7-Tridecadienyl acetate,(4E,7Z), 68 3-Tridecenyl acetate,@), 23 3,3,7-Trimethyl-2,9dioxatricyclo[3.3 I 04.’]nonane, 436 3,7, I I-Trimethyl-1,3,6,10dodecatetraene,(3E,3Z,6E),273 3,7,1 I-Trimethyl-2,4,6,10dodecatetraene,(2Z,42,62),276 3,7,1 I-Trimethyldodeca-2,6,10trienal,(ZE,6E), 336 3,7,1 l-Trimethyldodeca-2,6,10trienal,(22,6E), 336 15,19,23-Trimethylheptatriacotane, 13 6,10,13-Trimethyl-l-tetradecanol, 128 I ,2,6-Trimethyltetradecyl acetate, 122 I ,2,6-Trimethyltetradecyl propanoate, 122 24-Tritriaconten-2-one,(Z),175 Trogodermal,(R,E), I52 Trogodermal,(R,Z), 152 Trogodertna glabrum, 16 Trogodertna gratiariutn, 152, 16 Trogoderma species, 152 Trypodendron lineatutn, 435, 436 Tsetse fly, 12, 13 Turnip moth, 25 Tyrophagiis pictrescenriae, 29 I Ulretheisa ornatrix, 66, 83 7, IO-Undecadien-4-olide,(E),233 5-Undecenoic acid,(Z,E), 210 1,3,7,7-Tetramethyl-2-oxabicyclo[4.4.0]dec-9-6-Undecen-2-01,(2), I I en-S-one,(lR*,3S*,6R*), 380 5-Undecen-2-one,(Z), 157 3,4,7, I l-TetramethyI-6,lOtridecadienal,(3S,4R,6E,IOZ), 148 4,6,10,12-Tetramethyl-2,4-trideradien-7- Varied carpet beetle, 210 one,(2E,4E), 184 Velvetbean caterpillar moth, 82 Tetramoriurn iwipuruni, 10 I Vespa orientalis, 242 Thamnophis sirtalis parietalis, 175 Vetch aphid, 364 Thaumetopoea processionea, 63 Viraceapolistiforttiis, 74 531 532 Subject Index Wax moth, 138 Western balsam bark beetle, 394 Western corn rootworm, 113 Western pine beetle, 381, 394 Western tent caterpillar, 131 White peach scale, 330 White pine sawfly, 128 Wild silk moth, 70 Winter moth, 81 Xylocopa hirsutissima, 220 Xylorrechus pyrrhoderus, 109, 19 I Yellow mealworm, 1 Yellow peach moth, 133 Yellow scale, 326 Zeuzera pyrina, 14 The Total Synthesis of Natural Products, Volume9 Edited by John ApSlmon Copyright © 1992 by John Wiley & Sons, Inc Fomula Index 533 534 Formula Index ... Canada November 199 1 vii Contents The Synthesis of Insect Pheromones, 197 9- 198 9 KENJIMORI Subject Index 523 Formula Index 533 ix The Total Synthesis of Natural Products, Volume9 Edited by John... (CHJ12Me 19 Scheme 39 Organoborane chemistry was extensively used for the synthesis of 19 In Brown’s first synthesis of 19, base-induced iodination of a vinylborane A provided 19 (Scheme 40) .95 -96 The. . .THE TOTAL SYNTHESIS OF NATURAL PRODUCTS The Total Synthesis of Natural Products VOLUME Edited by John ApSimon Ottawa-Carleton Institute