The Total Synthesis of Natural Products, Volumes 10 and 11, 2 Volume Set

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

• ISBN13: 9780471194071
• ISBN10: 0471194077
• Edition: 1st
• Format: Hardcover
• Copyright: 1999-06-18
• Publisher: Wiley-Interscience

Summary

The indispensable reference for the twenty-first century chemist...

A fascinating and comprehensive look into one of chemistry's fastest growing specialties--sesquiterpene synthesis--Volume Ten of The Total Synthesis of Natural Products focuses on acyclic and monocyclic compounds and sheds light on the structure and makeup of this important class of hydrocarbons.

A useful and practical tool for researchers interested in locating any of the major classes of sesquiterpene compounds, the author will also provide, if needed, a database to the more than 1,600 articles on sesquiterpene synthesis. The ultimate index to the newest experimental work in synthetic chemistry, this latest volume in The Total Synthesis of Natural Products series is also a glossary to the new language of chemistry in the next century.

Look for the following related title in the series:

THE TOTAL SYNTHESIS OF NATURAL PRODUCTS, Volume Eleven

Volume Eleven continues the authoritative coverage on sesquiterpene synthesis begun in Volume Ten, examining compounds with bicyclic and tricyclic ring structures., 1997 (0-471-18874-3)

The research on the synthesis of sesquiterpenes, derivatives of terpenes, a class of hydrocarbons commonly found in oils, resins, and balsams, has grown exponentially over the past fifteen years. With over 500 sesquiterpene syntheses already developed, the literature on this experimental specialty is voluminous, now encompassing over 1,600 re-search papers. Volume Ten in The Total Synthesis of Natural Products provides a systematic and comprehensive look at acyclic and monocyclic compounds in sesquiterpene synthesis.

Reflecting one of the significant changes in sesquiterpene re-search, that is, the increase in compound targets prepared in an optically active form, the present volume includes their absolute configurations, signs of optical rotation, or both.

This newest volume in The Total Synthesis of Natural Products series is an "A-to-Z" look at acyclic and monocyclic compounds in sesquiterpene synthesis, one of the most dynamic areas in the ongoing revolution in chemical synthesis, and is a must for the chemical professional.

Author Biography

David Goldsmith, Consultant Nephrologist, Renal Unit, Guy's Hospital, London and Hon Snr lecturer,GKT, King's College, London. He is also involved in developing a renal specialist library as part of the NHS Information Executive National Elect Library Project.

Michael Pirrung is an organic chemist with research in the areas of chemical biology, synthesis, and nucleic acids. He trained in the labs of Clayton Heathcock at UC-Berkeley and Gilbert Stork at Columbia. He is a pioneer in the field of microarrays, which have important biological applications in genomics.

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