Riassunto
This series stemmed from a group of weekly seminars in our research group aimed at keeping its members abreast of recent developments in organic synthesis. The seminars tended to consist of several syntheses of natural products or related systems with particular emphasis on the general strategy inherent in the effort, new and interesting reactions which were utilized in the work, and specificity (or the lack of it) in arranging the relative stereochemistry of asymmetric centers and the geometry of double bonds. We found that natural products offered an attractive setting in which the larger science of organic chemistry could be put to crucial tests. A truly elegant synthesis is a major advance in that it epitomizes how an imaginative mastery of the course of organic reactions can achieve a sophisticated objective by an economy of operations. Indeed any successful synthesis of a reasonably complex product, however cumbersome and graceless, is an important event for those who delight in the problem-solving dimension of science.
Contenuti
I. Alkaloids and Intermediates in the Synthesis of Alkaloids.- 1. Acronycine.- 2. Ajaconine and Atidine Intermediates.- 3. Androcymbine-Type Compounds.- 4. Apoferrorosamine and Myosmine.- 5. 6,7-Benzomorphan.- 6. Condyfoline, Tubifoline, and Tubifolidine.- 7. Coreximine.- 8. (-)-Corynantheidine.- 9. (3S, 15S, 20R)-Corynantheine.- 10. Dasycarpidone and Epidasycarpidone.- 11. Dasycarpidone and Epidasycarpidone.- 12. Dihydrocrinine and Dihydrovittatine.- 13. Dihydrogambirtannine and Aspidosperma-Strychnos Alkaloid Models.- 14. 15,16-Dimethoxyerythrinan-3-One.- 15. Synthetic Approaches to Diterpene Alkaloids.- 16. Diterpene Alkaloid Intermediates.- 17. Diterpene Alkaloids.- 18. Epiibogamine and Ibogamine.- 19. Epiibogamine.- 20. Synthesis of Ring Systems Related to Hasubanan Alkaloids.- 21. Hernadine.- 22. Homoerythrinadienone.- 23. Homoproaporphine-Type Compounds.- 24. ?,?-Disubstituted Indoline Derivatives.- 25. 17-Acetyl-5?-Etiojerva-12,14,16-Trien-3?-OL.- 26. Lupinine and Epilupinine and the Hydrolulolidine and Hydrojulolidine Ring Systems.- 27. 12-Epilycopodine.- 28. Lycopodine.- 29. Lycopodine.- 30. Mesembrine.- 31. Mesembrine.- 32. Mesembrine.- 33. Mesembrine.- 34. Mesembrine.- 35. Ochotensine and Ochotensimine.- 36. Ochotensimine.- 37. Perlolidine.- 38. Petaline.- 39. Quebrachamine Skeleton.- 40. Sanguinarie.- 41. Sempervirine Hydrobromide.- 42. Solanidine.- 43. Stebisimine.- 44. Veatchine.- 45. Velbanamine.- 46. Verarine.- 47. Monomeric Vinca Alkaloids-Vincadine, Vincaminoreine, Vincaminorine, Vincadifformine, and Minovine.- 48. Dimeric Vinca Alkaloids.- 49. Vincaminol.- 50. 1-Methyl-16-Demethoxycarbonyl-20-Desethylidene-Vobasine.- 51. Withasomnine.- 52. Withasomnine.- II. Terpenes and Related Structures.- A. Monoterpenes.- 1. Actinidiolide, Dihydroactinidiolide, and Actinidol.- 2. Nezukone.- 3. Rosefuran and Dehydroelsholtzione.- 4. Verbenalol.- 5. Sabinene, Sabina Ketone, and Sabinene Hydrate.- B. Sesquiterpenes.- 1. Abscisic Acid.- 2. Juvabione.- 3. Andrographolide Lactone.- 4. AR-Himachalene.- 5. Bulnesol.- 6. Carabrone.- 7. Eremophilene and Eremoligenol.- 8. Eremophil-3,11-Diene.- 9. Tetrahydroeremophilone.- 10. ?-Eudesmol.- 11. Dehydrofuropelargones.- 12. Isoiresin, Dihydroiresin, and Isodihydroiresin.- 13. Juniper Camphor and Selin-11-En-4?-Ol.- 14. Nootkatone.- 15. Valeranone.- 16. ?-Vetivone.- 17. Nor-Ketoagarofuran.- 18. ?-Agarofuran and ?-Agarofuran.- 19. ?’(10)-Aristolene.- 20. Aristolone.- 21. 4-Demethylaristolone.- 22. ?-Bourbonene and ?-Bourbonene.- 23. ?-Bourbonene.- 24. A Functionalized Illudane.- 25. Illudin M.- 26. Lindestrene.- 27. Patchouli and Epipatchouli Alcohols.- 28. Sativene.- C. Diterpenes.- 1. Methyl Deisopropyldehydrobietate.- 2. Carnosol Dimethyl Ether and Carnosic Acid Dimethyl Ether.- 3. Ferruginol.- 4. Fichtelite.- 5. Kaur-16-En-19-OIC Acid.- 6. Methyl-2-Hydroxy-1,1,4a-Trimethyl-7-Oxoperhydrophenan-Threne-8a-Carboxylate.- 7. 10-Cyano-12-Hydroxy-7-Oxo-17-Norpodocarpa-5,8,11,13-Tetraene.- 8. Desoxypodocarpic Acid and 13-Methoxypodocarpic Acid.- 9. Podocarpic Acid.- 10. Sandaracopimaric Acid.- 11. Methyl Trachylobanate.- D. Triterpenes.- 1. ?-Amyrine.- 2. Cycloartenol.- III. Other Natural Products.- A. Antibiotics and Metabolites.- 1. Anthramycin.- 2. Cyclopenin.- 3. 6-Demethyl-6-Deoxytetracycline.- 4. Terramycin.- 5. Dihydroradicinin.- 6. Fulvoplumierin.- 7. Geosmin.- 8. Indolmycin.- 9. Kasugamycin.- 10. 5,6-Trans-Penicillin V Methyl Ester.- 11. Pyrethrolone.- 12. Rhodoquinone.- B. Cannabinols.- 1. Alloevodionol, Cannabichromene, and Franklinone.- 2. Cannabichromene and Cannabicyclol.- 3. ?6a,10a-Tetrahydrocannabinol.- 4. Tetrahydrocannabinol Congener.- C. Juvenile Hormones and Propylure.- 1. Stereospecific Approach to Juvenile Hormones.- 2. Cecropia Juvenile Hormone.- 3. Cecropia Juvenile Hormone.- 4. Propylure.- D. Porphyrins.- 1. Deoxophylloerythroetioporphyrin.- 2. Octaethylporphyrin.- 3. Synthesis of Oxyporphyrins.- E. Prostaglandins.- 1. Prostaglandins E1, A1, F1?, and F1?.- 2. Prostaglandins of the E1 and F1 Series.- 3. Prostaglandins.- 4. 7-Oxaprostaglandin F1?.- F. Steroids and Related Systems.- 1. (-)-17?-Hydroxy-?9(10)dES A-Androsten-5-One.- 2. 3-Methoxy-17?-Carboxyoestra-1,3,5(10),6,8-Pentaene.- 3. Retroprogesterone and Dehydroretroprogesterone.- 4. Estrone.- 5. 16,17-Dehydroprogesterone.- G. Zearalenones.- 1. Dideoxyzearalane.- 2. Zearalenone.- 3. Zearalenone.
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