Description

Book Synopsis
These two volumes provide a comprehensive look into one of chemistry's fastest growing specialities - sesquiterpene synthesis. They provide a useful and practical tool for researchers interested in locating any of the major classes of sesquiterpene compounds.

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

The Total Synthesis of Natural Products Volumes

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    A Hardback by David Goldsmith, Michael C. Pirrung, Andrew T. Morehead

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      Publisher: John Wiley & Sons Inc
      Publication Date: 07/07/1999
      ISBN13: 9780471194071, 978-0471194071
      ISBN10: 0471194077

      Description

      Book Synopsis
      These two volumes provide a comprehensive look into one of chemistry's fastest growing specialities - sesquiterpene synthesis. They provide a useful and practical tool for researchers interested in locating any of the major classes of sesquiterpene compounds.

      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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