The Total Synthesis of Natural Products, Volume 11, Part B Bicyclic and Tricyclic Sesquiterpenes,9780471188742

The Total Synthesis of Natural Products, Volume 11, Part B Bicyclic and Tricyclic Sesquiterpenes

by ; ; ;
Edition: 1st
ISBN13: 9780471188742
ISBN10: 0471188743
Format: Hardcover
Pub. Date: 1999-05-26
Publisher(s): Wiley-Interscience
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Summary

A complement to this work, Volume Ten examines compounds with acyclic and monocyclic ring structures in sesquiterpene synthesis. 1997 (0-471-59679-5) 173 pp.

Author Biography

DAVID GOLDSMITH, PhD, is Pro- fessor of Chemistry at Emory University in Atlanta, Georgia. He is former Chair of the Emory Chemistry Department and has been Visiting Professor at Stras-bourg, Mulhouse, and Grenoble. Professor Goldsmith received his PhD in organic chemistry from Columbia University. His research interests have been principally in the field of natural product synthesis.

Table of Contents

Acknowledgments xi
Introduction xiii
Reagent Glossary xv
III. BICYCLIC SESQUITERPENES 1(274)
Eudesmanes
1(32)
β-Eudesmol, α-Eudesmol, Intermediol, Neointermediol, Amiteol, Cycloeudesmol, Maaliol, α-Selinene, β-Selinene, γ-Selinene, Selinadiene, AE 1, Vetiselinene
1(9)
β-Dictyopterol, Selin-4(15)-ene-1β,11-diol, Balanitol, Occidentalol, Isochamaecynone, Chamaecynone, Emmotin-G, Occidol
10(4)
Amitermes Defensive Substance, Isocelorbicol
14(1)
α-Cyperone, β-Cyperone, Carissone
15(2)
Eudesma-4(14),7(11)-diene-8-one, Arctiol, β-Costol, β-Costal, Isocostic Acid, 3-Oxoisocostic Acid, 1-Oxocostic Acid
17(3)
α-Costal, 7-Hydroxycostol, 7-Hydroxycostal
20(1)
3-Oxoeudesmatrienoic Acid, 12,15-Dioxaselina-4,11-diene
21(1)
Junenol, Acolamone
22(1)
Atractylon, Lindestrene, Tubipofuran
23(2)
Glutinosone
25(1)
Dehydroasterolide, Dihydrocallitrisin, Isoalantolactone, Septuplinolide, Ivalin, Oxodiplophyllin, Yomogin
25(4)
Frullanolide, Tuberiferin, Deoxybrachylaenolide, Gazanolide, Arbusculin D, 3-Oxo-11-hydroxyeudesmadienolide, Magnolialide, Maritimin, Dihydrosantamarine, α-Santonin
29(4)
Cadinanes
33(21)
Calamenene, Hydroxycalamenenes, Methoxycalamenenes
33(5)
Mansonones, Perezinone
38(1)
7,8-Dihydroxy-11,12-dehydrocalamenene, Heritol
39(2)
Lacinilene C
41(1)
α-Cadinene, γ2-Cadinene, ϵ-Cadinene, ϵ-Muurolene, β-Cadinene, δ-Cadinene
42(4)
Zonarene, Dihydropernetic Acid B, Veticadinol, Torreyol, Isocalamenediol, Cubenol, Epicubenol
46(4)
1,4-Epoxycadinane, Verboccidentafuran, Hibiscone, Arteannuin B
50(2)
Halipanicine, Sclerosporin, Sclerosporal, Khusilal
52(2)
Drimanes
54(16)
Bicyclofarnesic Acid, Drimenol, Albicanyl Acetate, Albicanol, Farnesiferol A
54(3)
Euryfuran, Valdiviolide, Confertifolin, Isodrimenin, Cinnamolide, Polygodial, Drimenin
57(5)
Fragrolide, Cinnamodial, Warburganal, Isotadeonal, Muzigidial, Colorata-4(13),8-dienolide, 3β-Acetoxydrimenin, Pereniporin A, Pereniporin B
62(6)
Driman-8,11-diol, Drim-9(11)-en-8-ol, 7-Oxo-11-nordrimen-8-en-12-oic Acid, 1,1,5,6-Tetramethyltetralin
68(2)
Eremophilanes
70(9)
Nootkatone, Valencene, Isovalencenic Acid, Isovalencenol, Eremoligenol, Eremophilene, Valerianol, Eremophilone, Dehydrofukinone, Aristolone, Isopetasol, Petasol, Petasitolone
70(5)
Phomenone, Eremofortin B, Sporogen-AO 1
75(2)
Ligularenolide, Ligularone, Petasalbine, Eremophilenolide, Furanoeremophilone, Furanoeremophilan-14,6a-olide
77(2)
Miscellaneous Hydronaphthalenes
79(18)
Acetyldehydrorishitinol, Cinalbicol, 4-Methoxyisocadalene, 4-Hydroxyisocadalene, 1-Hydroxyisocadal-4-one, 2-Methoxy-7-norcalamenene, Maturone, Platyphyllide
79(4)
Ambrox, Pallescensin A
83(4)
Furodysin, Furodysinin
87(1)
Lemnal-5a-en-2-one, Kanshone A, Nardosinone
88(3)
Valerane, Valeranone, Cryptofauronol, Fauronyl Acetate
91(3)
Isoacanthodoral, Nanaiomoal
94(2)
Thujopsene
96(1)
Fused Ring Compounds: 6,3
97(4)
Sirenin, Sesquicarene, Isosesquicarene
97(4)
Fused Ring Compounds: 6,5
101(25)
Pterosins
101(2)
Pacifigorgiol, Tamariscol
103(1)
Brasilenol, Conocephalenol
104(1)
Axamide-1, Axisonitrile-1, Axamide-4, Axisonitrile-4, Axisothiocyanate-4, Oppositol
105(2)
Pinguisone, Deoxopinguisone
107(2)
Alliacolide
109(2)
Chiloscyphone
111(1)
Coriamyrtin, Asteromurin, Picrotoxinin, Picrotin
112(4)
Oplopanone, Anhydrooplopanone
116(1)
Bakkenolide A, Homogynolide A, Homogynolide B, Palmosalide C
117(4)
Thapsane
121(1)
Valerenal
121(2)
8-Deoxyanisatin, Anisatin, Neoanisatin, Noranisatin
123(2)
Isovelleral, Stearoylvelutinal
125(1)
Marmalerin
125(1)
Fused Ring Compounds: 6,7
126(6)
ar-Himachalene, α-Himachalene, β-Himachalene, γ-Himachalene
126(3)
Perforenone, Guadalupol, Epiguadalupol, Perforene
129(1)
Widdrol
130(1)
Pallescensin E, Pallescensin F, Pallescensin G
131(1)
Fused Ring Compounds: 6,8
132(2)
Neolemnane, Neolemnanyl Acetate, Parvifolin
132(2)
Fused Ring Compounds: 5,7
134(34)
Lettucenin A
134(1)
β-Bulnesene, α-Bulnesol
135(2)
Gnididione
137(1)
Curcumenol, Curcumol
138(1)
Liguloxide, Kessane
139(1)
Alismol
140(1)
Guaianolides: Compressanolide, Estafiatin
141(1)
Guaianolides: Arborescin, 3-Epizaluzanin C, Zaluzanin C, Mokko Lactone, Dehydrocostus Lactone, Eremanthin
142(3)
Guaianolides: Grosshemin, Oxoisodehydroleucodin, Jalcagauianolide
145(2)
Pseudoguaianolides: Ambrosanolides-Confertin, Rudmollin
147(5)
Pseudoguaianolides: Helananolides-Aromatin, Aromaticin, Graveolide, Fastigilin C, Carpesiolin
152(3)
Daucene, Aspterric Acid
155(2)
Mintsulfide, Aphanamol-I, 2-Oxoisodauc-5-en-12-al
157(2)
Furanol, Furanether A, Furanether B, Furandiol, Lactarorufin A, Furoscrobiculin B
159(2)
Africanol
161(2)
Spathulenol, Alloaromadendrane-4α, 10α-diol, Cyclocolorenone, Didehydroaromadendrane
163(2)
Clavukerin A, Clavukerin C, Clavularin A and B
165(3)
Fused Ring Compounds: 5,8
168(6)
Precapnelladiene
168(3)
Poitediol
171(1)
Dactylol
172(2)
Asteriscanolide
174(1)
Fused Ring Compounds: 4,9
174(3)
Isocaryophyllene, Caryophyllene
175(2)
Punctaporonin B
177(1)
Fused Ring Compounds: 5,5
177(9)
Pentalenolactone E
178(4)
Pentalenolactone, Pentalenolactone G, Pentalenolactone H, Pentalenolactone P
182(4)
Isolated Rings
186(39)
Cuparene, Herbertene, Tochuinol
186(5)
α-Cuparenone, β-Cuparenone
191(8)
Laurene, Epilaurene, Isolaurene
199(3)
Allolaurinterol, Cyclolaurene
202(2)
Aplysin, Filiformin, Aplysinol, Isoaplysin
204(3)
Trichodiene, Bazzanene
207(7)
Trichodermol, Verrucarol
214(3)
Calonectrin, Anguidine
217(3)
12,13-Epoxytrichothec-9-ene, 15-Hydroxytrichothec-9,12-diene
220(2)
Neosporol, Sporol
222(2)
Dihydrofomannosin Acetate, Fomannosin
224(1)
Spirocyclic Systems
225(29)
Acoradiene, α-Acoradiene, Acoratriene, β-Acorenol, β-Acoradiene
225(4)
Acorone, Acorenone, Acorenone B
229(5)
Hinesol, Agarospirol, α-Vetispirene, β-Vetispirene
234(5)
β-Vetivone, Anhydro-β-rotunol
239(3)
Solavetivone, 15-nor-Solavetivone, 3-Hydroxysolavetivone, Aglycone A3, Lubimin, Oxylubimin, Isolubimin, Lubiminol
242(5)
Vitrenal
247(2)
Spirolaurenone
249(1)
Erythrodiene
249(1)
Cinera-5,7,11-trien-9-one
250(1)
α-Chamigrene, β-Chamigrene, Bromomethylenechamigreone
251(3)
Bridged Systems
254(21)
β-Santalol, β-Santalene, epi-β-Santalene, α-Santalol, α-Santalene
254(8)
α-cis-Bergamotene, β-cis-Bergamotene, β-trans-Bergamotene, (E)-endo-α-Bergamoten-12-oic acid, (E)-endo-β-Bergamoten-12-oic acid, Pinthunamide
262(3)
Helminthosporal
265(1)
Upial
266(2)
Nakafuran-8, Nakafuran-9, Dihydropallescensin
268(2)
Dihydrospiniferin-1, Spiniferin-1
270(5)
IV. TRICYCLIC SEQUITERPENES 275(181)
Angular Triquinanes
275(30)
Isocomene
275(5)
Silphinene, 8-Oxo-silphinene
280(6)
Pentalenene, Pentalenic Acid
286(10)
Silphiperfolenes, Methyl Cantabrenonate, Subergorgic Acid
296(9)
Propellanes
305(6)
Modhephene
305(6)
Linear Triquinanes
311(46)
Hirsutene
312(13)
Capnellenes
325(18)
Coriolin, Hypnophilin
343(11)
Hirsutic Acid C, Cerotopicanol
354(3)
Miscellaneous Fused Tricyclic Sesquiterpenes
357(13)
β-Bourbonene, Panasinsene, Italicene
357(3)
Protoillud-6-ene, 8-Hydroxy-protoillud-6-ene, Illudol
360(3)
Punctatin A, Ptaquilosin, Illudin M
363(3)
Sterpuric Acid, Sterpurene-3,12,14-triol, Sterpurene
366(4)
Bridged Tricyclic Sesquiterpenes
370(86)
Khusimone, Zizaene, Zizanoic acid, Prezizaene, Prezizanol, Jinkohol
370(7)
Patchouli alcohol, Norpatchoulenol, Seychellene, Cycloseychellene
377(5)
Longifolene, Culmorin, Longiborneol
382(4)
Copacamphor, Ylangocamphor, Cyclosativene, Sativene, cis-Sativenediol, Sinularene, Acetoxysinularene
386(8)
Quadrone
394(12)
Cedrene, Isocedrenes, 8,14-Cedranoxide, 8,14-Cedranediol, Biotol, Pipitzols
406(8)
α-Copaene, β-Copaene, β-Ylangene, Lemnalol, Longipinene
414(2)
9-Isocyanopupukeanane
416(2)
Gymnomitrol
418(1)
Secoishwaranol, Ishwarane
419(1)
Rhodolauradiol, Khusiol
420(2)
Epilogue
422(1)
References
423(33)
Skeleton Index 456(5)
Author Index 461(5)
Subject Index 466

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