Total Synthesis of Natural Products / Edition 1

Total Synthesis of Natural Products / Edition 1

by David Goldsmith, Michael C. Pirrung, Andrew T Morehead, Jr.
     
 

ISBN-10: 0471194077

ISBN-13: 9780471194071

Pub. Date: 05/28/1999

Publisher: Wiley

This is the latest volume in a series on the reported total syntheses of various groups to natural products, with commentary on the strategy involved and with emphasis on any stereochemical control. Volume 10 studies the total synthesis of sesquiterpenes.  See more details below

Overview

This is the latest volume in a series on the reported total syntheses of various groups to natural products, with commentary on the strategy involved and with emphasis on any stereochemical control. Volume 10 studies the total synthesis of sesquiterpenes.

Product Details

ISBN-13:
9780471194071
Publisher:
Wiley
Publication date:
05/28/1999
Series:
Total Synthesis of Natural Products Series, #12
Pages:
690
Product dimensions:
6.30(w) x 9.37(h) x 2.02(d)

Table of Contents

Acknowledgments

Introduction

Reagent Glossary

III. Bicyclic Sesquiterpenes

A. Eudesmanes

1. β-Eudesmol, α-Eudesmol, Intermediol, Neointermediol, Amiteol, Cycloeudesmol, Maaliol, α-Selinene, β-Selinene, γ-Selinene, Selinadiene, AE 1, Vetiselinene

2. β-Dictyopterol, Selin-4(15)-ene-1β, 11-diol, Balanitol, Occidentalol, Isochamaecynone, Chamaecynone, Emmotin-G, Occidol

3. Amitermes Defensive Substance, Isocelorbicol

4. α-Cyperone, β-Cyperone, Carissone

5. Eudesma-4(14),7(11)-diene-8-one, Arctiol, β-Costol, β-Costal, Isocostic Acid, 3-Oxoisocostic Acid, 1-Oxocostic Acid

6. α-Costal, 7-Hydroxycostol, 7-Hydroxycostal

7. 3-Oxoeudesmatrienoic Acid, 12,15-Dioxaselina-4,11-diene

8. Junenol, Acolamone

9. Atractylon, Lindestrene, Tubipofuran

10. Glutinosone

11. Dehydroasterolide, Dihydrocallitrisin, Isoalantolactone, Septuplinolide, Ivalin, Oxodiplophyllin, Yomogin

12. Frullanolide, Tuberiferin, Deoxybrachylaenolide, Gazanolide, Arbusculin D, 3-Oxo-11-hydroxy-eudesmadienolide, Magnolialide, Maritimin, Dihydrosantamarine, α-Santonin

B. Cadinanes

1. Calamenene, Hydroxycalamenenes, Methoxycalamenenes

2. Mansonones, Perezinone

3. 7,8-Dihydroxy-11,12-dehydrocalamenene, Heritol

4. Lacinilene C

5. α-Cadinene, γ2-Cadinene, ε-Cadinene, ε-Muurolene, β-Cadinene, δ-Cadinene

6. Zonarene, Dihydropernetic Acid B, Veticadinol, Torreyol, Isocalamenediol, Cubenol, Epicubenol

7. 1,4-Epoxycadinane, Verboccidentafuran, Hibiscone, Arteannuin B

8. Halipanicine, Sclerosporin, Sclerosporal, Khusilal

C. Drimanes

1. Bicyclofarnesic Acid, Drimenol, Albicanyl Acetate, Albicanol, Farnesiferol A

2. Euryfuran, Valdiviolide, Confertifolin, Isodrimenin, Cinnamolide, Polygodial, Drimenin

3. Fragrolide, Cinnamodial, Warburganal, Isotadeonal, Muzigidial, Colorata-4(13),8-dienolide, 3β-Acetoxydrimenin, Pereniporin A, Pereniporin B

4. Driman-8,11-diol, Drim-9(11)-en-8-ol, 7-Oxo-11-nordrimen-8-en-12-oic Acid, 1,1,5,6-Tetramethyltetralin

D. Eremophilanes

1. Nootkatone, Valencene, Isovalencenic Acid, Isovalencenol, Eremoligenol, Eremophilene, Valerianol, Eremophilone, Dehydrofukinone, Aristolone, Isopetasol, Petasol, Petasitolone

2. Phomenone, Eremofortin B, Sporogen-AO 1

3. Ligularenolide, Ligularone, Petasalbine, Eremophilenolide, Furanoeremophilone, Furanoeremophilan-14,6a-olide

E. Miscellaneous Hydronaphthalenes

1. Acetyldehydrorishitinol, Cinalbicol, 4-Methoxyisocadalene, 4-Hydroxyisocadalene, 1-Hydroxyisocadal-4-one, 2-Methoxy-7-norcalamenene, Maturone, Platyphyllide

2. Ambrox, Pallescensin A

3. Furodysin, Furodysinin

4. Lemnal-5a-en-2-one, Kanshone A, Nardosinone

5. Valerane, Valeranone, Cryptofauronol, Fauronyl Acetate

6. Isoacanthodoral, Nanaiomoal

7. Thujopsene

F. Fused Ring Compounds: 6,3

1. Sirenin, Sesquicarene, Isosesquicarene

G. Fused Ring Compounds: 6,5

1. Pterosins

2. Pacifigorgiol, Tamariscol

3. Brasilenol, Conocephalenol

4. Axamide-1, Axisonitrile-1, Axamide-4, Axisonitrile-4, Axisothiocyanate-4, Oppositol

5. Pinguisone, Deoxopinguisone

6. Alliacolide

7. Chiloscyphone

8. Coriamyrtin, Asteromurin, Picrotoxinin, Picrotin

9. Oplopanone, Anhydrooplopanone

10. Bakkenolide A, Homogynolide A, Homogynolide B, Palmosalide C

11. Thapsane

12. Valerenal

13. 8-Deoxyanisatin, Anisatin, Neoanisatin, Noranisatin

14. Isovelleral, Stearoylvelutinal

15. Marmalerin

H. Fused Ring Compounds: 6,7

1. ar-Himachalene, α-Himachalene, β-Himachalene, γ-Himachalene

2. Perforenone, Guadalupol, Epiguadalupol, Perforene

3. Widdrol

4. Pallescensin E, Pallescensin F, Pallescensin G

I. Fused Ring Compounds: 6,8

1. Neolemnane, Neolemnanyl Acetate, Parvifolin

J. Fused Ring Compounds: 5,7

1. Lettucenin A

2. β-Bulnesene, α-Bulnesol

3. Gnididione

4. Curcumenol, Curcumol

5. Liguloxide, Kessane

6. Alismol

7. Guaianolides: Compressanolide, Estafiatin

8. Guaianolides: Arborescin, 3-Epizaluzanin C, Zaluzanin C, Mokko Lactone, Dehydrocostus Lactone, Eremanthin

9. Guaianolides: Grosshemin, Oxoisodehydroleucodin, Jalcagauianolide

10. Pseudoguaianolides: Ambrosanolides-Confertin, Rudmollin

11. Pseudoguaianolides: Helananolides-Aromatin, Aromaticin, Graveolide, Fastigilin C, Carpesiolin

12. Daucene, Aspterric Acid

13. Mintsulfide, Aphanamol-I, 2-Oxoisodauc-5-en-12-al

14. Furanol, Furanether A, Furanether B, Furandiol, Lactarorufin A, Furoscrobiculin B

15. Africanol

16. Spathulenol, Alloaromadendrane-4α,10α-diol, Cyclocolorenone, Didehydroaromadendrane

17. Clavukerin A, Clavukerin C, Clavularin A and B

K. Fused Ring Compounds: 5,8

1. Precapnelladiene

2. Poitediol

3. Dactylol

4. Asteriscanolide

L. Fused Ring Compounds: 4,9

1. Isocaryophyllene, Caryophyllene

2. Punctaporonin B

M. Fused Ring Compounds: 5,5

1. Pentalenolactone E

2. Pentalenolactone, Pentalenolactone G, Pentalenolactone H, Pentalenolactone P

N. Isolated Rings

1. Cuparene, Herbertene, Tochuinol

2. α-Cuparenone, β-Cuparenone

3. Laurene, Epilaurene, Isolaurene

4. Allolaurinterol, Cyclolaurene

5. Aplysin, Filiformin, Aplysinol, Isoaplysin

6. Trichodiene, Bazzanene

7. Trichodermol, Verrucarol

8. Calonectrin, Anguidine

9. 12,13-Epoxytrichothec-9-ene, 15-Hydroxytrichothec-9,12-diene

10. Neosporol, Sporol

11. Dihydrofomannosin Acetate, Fomannosin

O. Spirocyclic Systems

1. Acoradiene, α-Acoradiene, Acoratriene, β-Acorenol, β-Acoradiene

2. Acorone, Acorenone, Acorenone B

3. Hinesol, Agarospirol, α-Vetispirene, β-Vetispirene

4. β-Vetivone, Anhydro-β-rotunol

5. Solavetivone, 15-nor-Solavetivone, 3-Hydroxysolavetivone, Aglycone A3, Lubimin, Oxylubimin, Isolubimin, Lubiminol

6. Vitrenal

7. Spirolaurenone

8. Erythrodiene

9. Cinera-5,7,11-trien-9-one

10. α-Chamigrene, β-Chamigrene, Bromomethylenechamigrenone

P. Bridged Systems

1. β-Santalol, β-Santalene, epi-β-Santalene, α-Santalol, α-Santalene

2. α-cis-Bergamotene, β-cis-Bergamotene, β-trans-Bergamotene, (E)-endo-α-Bergamoten-12-oic acid, (E)-endo-β-Bergamoten-12-oic acid, Pinthunamide

3. Helminthosporal

4. Upial

5. Nakafuran-8, Nakafuran-9, Dihydropallescensin

6. Dihydrospiniferin-1, Spiniferin-1

IV. Tricyclic Sesquiterpenes

A. Angular Triquinanes

1. Isocomene

2. Silphinene, 8-Oxo-silphinene

3. Pentalenene, Pentalenic Acid

4. Silphiperfolenes, Methyl Cantabrenonate, Subergorgic Acid

B. Propellanes

1. Modhephene

C. Linear Triquinanes

1. Hirsutene

2. Capnellenes

3. Coriolin, Hypnophilin

4. Hirsutic Acid C, Cerotopicanol

D. Miscellaneous Fused Tricyclic Sesquiterpenes

1. β-Bourbonene, Panasinsene, Italicene

2. Protoillud-6-ene, 8-Hydroxy-protoillud-6-ene, Illudol

3. Punctatin A, Ptaquilosin, Illudin M

4. Sterpuric Acid, Sterpurene-3,12,14-triol, Sterpurene

E. Bridged Tricyclic Sesquiterpenes

1. Khusimone, Zizaene, Zizanoic acid, Prezizaene, Prezizanol, Jinkohol

2. Patchouli alcohol, Norpatchoulenol, Seychellene, Cycloseychellene

3. Longifolene, Culmorin, Longiborneol

4. Copacamphor, Ylangocamphor, Cyclosativene, Sativene, cis-Sativenediol, Sinularene, Acetoxysinularene

5. Quadrone

6. Cedrene, Isocedrenes, 8,14-Cedranoxide, 8,14-Cedranediol, Biotol, Pipitzols

7. α-Copaene, β-Copaene, β-Ylangene, Lemnalol, Longipinene

8. 9-Isocyanopupukeanane

9. Gymnomitrol

10. Secoishwaranol, Ishwarane

11. Rhodolauradiol, Khusiol

Epilogue

References

Skeleton Index

Author Index

Subject Index

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