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

by Pirrung, Michael C.; Morehead, Andrew T.; Young, Bruce G.; Goldsmith, David

• ISBN13: 9780471188742
• ISBN10: 0471188743
• Edition: 1st
• Format: Hardcover
• Copyright: 1999-05-26
• Publisher: Wiley-Interscience

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