Synthesis of a highly functionalized triquinane: Studies towards a total synthesis of subergorgic acid and its analogues

Molecules

Volumn 5, Issue 4, 2000, Pages 674-698

  Dragojlovic, Veljko ^a  

^a UNIVERSITY OF NORTH FLORIDA   (United States)

Author keywords

Bifunctional reagents; Methylenecyclopentane annulation; Sesquiterpenoid synthesis; Subergorgic acid; Triquinane synthesis

Indexed keywords

ALKADIENE; ALKANE DERIVATIVE; BROMIDE; COPPER; DIMETHYL SULFIDE; KETONE DERIVATIVE; NATURAL PRODUCT;

ALKYLATION; ARTICLE; GRIGNARD REACTION; REACTION ANALYSIS; SYNTHESIS;

EID: 0007548314     PISSN: 14203049     EISSN: None     Source Type: Journal    
DOI: 10.3390/50400674     Document Type: Article

References (54)

1. Paquette, L. A. The Development of Polyquinane Chemistry. Top. Curr. Chem. 1979, 79, 41-165.
2. Paquette, L. A. Recent Synthetic Developments in Polyquinane Chemsitry. Top. Curr. Chem. 1984, 119, 1-160.
3. Paquette, L. A.; Doherty, A. M. Polyquinane Chemistry. Reactivity and Structure Concepts in Organic Chemistry 1987, 26, 1-225.
4. Mehta, G.; Srikrishna, A. Synthesis of Polyquinane Natural Products: An Update. Chem. Rev. 1997, 97, 671-719.
5. Groweiss, A.; Fenical, W.; Cun-heng, H.; Clardy, J.; Zhongde, W.; Zhongnian, Y.; Kanghou, L. Subergorgic Acid, A Novel Tricyclopentanoid Cardiotoxin from the Pacific Gorgonian Coral Subergorgia Suberosa. Tetrahedron Lett. 1985, 26, 2379-2382.
6. Parameswaran, P. S.; Naik, C. G.; Kamat, S. Y.; Puar, M. S.; Das, P.; Hegde, V. R. Studies on the Secondary Metabolites from the Indian Gorgonian Subergorgia suberosa: Isolation and Characterization of Four Analogues of the Cardiotoxin Subergorgic Acid. J. Nat. Prod. 1998, 61, 832-834 and 1074.
7. Chen, B.-H.; Jiao, K.-F.; Ji Q.-E.; Song, H.-Q. Studies on the Relationship between the MO Indices and Anticholinesterase Activity of Subergorgin. Journal of Molecular Structure (Teochem) 1989, 188, 167-174.
8. Tan, X.; Ye, H.; Zeng, L.; Cui, Z.; He, S. An Organophosphorus (Soman) Antidote from Gorgonian Coral Subergorgia Suberosa. Zhongguo Haiyang Yaowu 1990, 9, 11-12 (Chemical Abstracts 1991, 115: 35564g).
9. Tan, X.; Ye, H.; Zeng, L.; Cui, Z.; He, S. An Organophosphorus (Soman) Antidote from Gorgonian Coral Subergorgia Suberosa. Zhongguo Haiyang Yaowu 1990, 9, 11-12 (Chemical Abstracts 1991, 115: 35564g).
10. Trost, B. M. Some Aspects of Organosulfur-Mediated Synthetic Methods. Acc. Chem. Res. 1978, 453-461.
11. 9(12)-Capnellene. Tetrahedron 1989, 45, 1089-1104.
12. Piers, E.; Karunaratne, V. Bifunctional Reagents in organic Synthesis. Total Synthesis of the Ses-quiterpenoids (±)-Pentalene and (±)-9-epi-Pentalene. Can. J. Chem. 1989, 67, 160-164.
13. Piers, E.; Reanud, J. Annulations via Bifunctional Reagents. Total Synthesis of (±)-Methyl Cantabrenonate and (±)-Methyl Epoxycantabrenonate. Synthesis 1992, 74-82.
14. Iwata, C.; Takemoto, Y.; Doi, M.; Imanishi, T. Stereoselective Total Synthesis of (±)-Subergorgic Acid, A New Type of Angular Triquinane Sesquiterpene. J. Org. Chem. 1988, 53, 1623-1628.
15. Wender, P.; deLong, M. Synthetic Studies on Arene-Olefin Cycloadditions. XII. Total Synthesis of (±)-Subergorgic Acid. Tetrahedron Lett. 1990, 31, 5429-5432.
16. Crimmins, M.; Dudek, C.; Cheung, A. W.-H. A Fragmentation-Rearrangement Sequence of Cyclobutylcarbinyl Radicals. Tetrahedron Lett. 1992, 33, 181-184.
17. Paquette, L. A.; Meister, P. G.; Friedrich, D.; Sauer, D. R. Enantioselective Total Synthesis of (-)-Subergorgic Acid. J. Am. Chem. Soc. 1993, 115, 49-56.
18. Piers, E.; Moss, N. Thermal Rearrangement of Divinylcyclopropane Systems. A New Formal Total Synthesis of (±)-Quadrone. Tetrahedron Lett. 1985, 26, 2735-2738.
19. Miller, R. D.; McKaen, D. R. The Facile Silylation of Aldehydes and Ketones using Trimethylsilyl Iodide: An Exceptionally simple Procedure for the Generation of Thermodinamically Equilibrated Trimethylsilylenol Ethers. Synthesis 1979, 730-732.
20. Ito, Y.; Hirao, T.; Saegusa, T. Synthesis of α,β-Unsaturated Carbonyl Compounds by Palladium(II)-Catalyzed Dehydrosilylation of Silyl Enol Ethers. J. Org. Chem. 1978, 43, 1011-1013.
21. Piers, E.; Chong, J. M. Regioselective Addition of Trimethylstannylcopper-Dimethyl sulphide to 1-Alkynes: Synthesis of ω-Substituted 2-(Trimethylstannyl)-1-Alkenes. J. Chem. Soc. Chem. Commun. 1983, 934-935.
22. Piers, E.; Karunaratne, V. 4-Chloro-2-lithio-1-butene, a Novel Donor-Acceptor Conjuctive Reagent. J. Org. Chem. 1983, 48, 1774-1776.
23. Taylor, R. J. K. Organocopper Conjugate Addition-Enolate Trapping Reactions. Synthesis 1985, 364-392.
24. Robins, M. J.; Wilson, J. S. Smooth and Efficient Deoxygentation of Secondary Alcohols. A General Procedure for the Conversion of Ribonucleosides to 2'-Deoxynucleosides. J. Am. Chem. Soc. 1981, 103, 932-933.
25. Robins, M. J.; Wilson, J. S.; Hansske, F. Nucleic Acids Related Compounds. 42. A General Procedure for the Efficient Deoxygenation of Secondary Alcohols. Regiospecific and Stereoselective Conversion of Ribonucleosides to 2'-Deoxynucleosides. J. Am. Chem. Soc. 1983, 105, 4059-4065.
26. Story, B.-A. The Total Synthesis of (±)-β-Panasinsene, Ph. D. Thesis, University of British Columbia, 1991, 87-92.
27. Brendel, J.; Weyerstahl, P. Total Synthesis of (±)-Silphiperfol-5- en-3-ol. Tetrahedron Lett. 1989, 30, 2371-2374.
28. Cram, D. J.; Abd Elhafez, F. A. Studies in Stereochemistry. X. The Rule of "Steric Control of Asymmetric Induction" in the Synthesis of Acyclic Systems. J. Am. Chem. Soc. 1952, 74, 5828-5835.
29. Chérest, M.; Felkin, H.; Prudent, N. Torsional Strain Involving Partial Bonds. The Stereochemistry of the Lithium Aluminium Hydride Reduction of Some Simple Open-Chain Ketones. Tetrahedron Lett. 1968, 2199-2204.
30. Wipke, W. T.; Gund, P. Simulation and Evaluation of Chemical Synthesis. Congestion: a Conformation-Dependent Function of Steric Environment at a Reaction Center. Application with Torsional Terms to Stereoselectivity of Nucleophilic Additions to Ketones. J. Am. Chem. Soc. 1976, 98, 8107-8118.
31. Wu, Y.-D.; Houk, K. N. Electronic and Conformational Effects of π-Facial Stereoselectivity in Nucleophilic Additions to Carbonyl Compounds. J. Am. Chem. Soc. 1987, 109, 908-910.
32. Wu, Y.-D.; Houk, K. N.; Trost, B. M. Origin of Enhanced Axial Attack by Sterically Undemanding Nucleophiles on Cyclohexanones. J. Am. Chem. Soc. 1987, 109, 5560-5561.
33. Wu, Y.-D.; Houk, K. N. Effect of Torsional Strain and Electrostatic Interactions on the Stereochemistry of Nucleophilic Additions to Cyclohexanone and Related Systems. Angew. Chem. Int. Ed. Engl. 1992, 31, 1019-1021.
34. Carlsen, P. H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. A Greatly Improved Procedure for Ruthenium Tetraoxide Catalyzed Oxidations of Organic Compounds. J. Org. Chem. 1981, 46, 3936-3938.
35. Corey, E. J.; Gross, A. W. Highly Selective, Kinetically Controlled Enolate Formation using Lithium Dialkylamides in the Presence of Trimethylchlorosilane. Tetrahedron Lett. 1984, 25, 495-498.
36. Ahmad, S.; Khan, M. A.; Iqbal, J. An Efficient Regio and Stereoselective Synthesis of Silyl Enol Ethers. Synth. Commun. 1988, 18, 1679-1683.
37. Tsuji, J.; Minami, I.; Shimizu, I. A Novel Palladium-Catalyzed Preparative Method of α,β-Unsaturated Ketones and Aldehydes from Saturated Ketones and Aldehydes via Their Silyl Enol Ethers. Tetrahedron Lett. 1983, 24, 5635-5638.
38. Minami, I.; Takahashi, K.; Shimizu, I.; Tsuji, J. New Synthetic Methods for α,β-Unsaturated Ketones, Aldehydes, Esters and Lactones by Palladium-Catalyzed reactions of Silyl Enol Acetates with Allyl Carbonates. Tetrahedron 1986, 42, 2971-2977.
39. Mincone, E.; Ortaggi, G.; Sirna, A. The Regioselective α,β-Dehydrogenation of Ketosteroids by Palladium(II) Chloride. Synthesis 1977, 773-774.
40. Barton, D. H. R.; Lester, D. J.; Ley, S. V. Dehydrogenation of Steriodal Ketones using Benzene-seleninic Anhydride. J. Chem. Soc. Chem. Commun. 1978, 130-131.
41. Barton, D. H. R.; Lester, D. J.; Ley, S. V. Dehydrogenation of Steriodal and Triterpenoid Ketones using Benzeneseleninic Anhydride. J. Chem. Soc. Perkin Trans I 1980, 2209-2212.
42. Barton, D. H. R.; Morzycki, J. W.; Motherwell, W. B.; Ley, S. V. Oxygen Atom Transfer from Iodylbenzene to Diphenyl Diselenides - A Convenient Method for Dehydrogenation of Steroidal 3-Ketones. J. Chem. Soc. Chem. Commun. 1981, 1044-1045.
43. Dragojlovic, V. Preparation of Cyclopentenones by Benzeneseleninic Anhydride Oxidation of Cyclopentanones. J. Chem. Res. (S) 1999, 256-257.
44. Lee, R. A.; McAndrews, C.; Patel, K. M.; Reusch, W. Methylation of Kinetically Generated Dienolate Anions Derived from α,β-Unsaturated Ketones. Tetrahedron Lett. 1973, 965-968.
45. Olofson, R. A.; Dougherty, C. M. Lithium 2,2,6,6-Tetramethylpiperidide and Related, Strong, Proton-Specific Bases. Evaluation in Synthesis. J. Am. Chem. Soc. 1973, 95, 582-584.
46. Bohlmann, F.; Jakupovic, J. Neue Sesquiterpen-Kohlenwasserstoffe mit Anomalen Kohlens-toffgerüst aus Silphium-Arten. Phytochemistry 1980, 19, 259-265 (the spectra have been erroneously reversed: Wender, P.; Singh, S. K. Synthetic Studies on Arene-Olefin Cycloadditions-VIII. Total Synthesis of (±)-Silphiperfol-6-ene, (±)-7αH-Silphiperfol-5-ene and (±)-7βH-Silphiperfol-5-ene. Tetrahedron Lett. 1985, 26, 5987-5990).
47. Bohlmann, F.; Jakupovic, J. Neue Sesquiterpen-Kohlenwasserstoffe mit Anomalen Kohlens-toffgerüst aus Silphium-Arten. Phytochemistry 1980, 19, 259-265 (the spectra have been erroneously reversed: Wender, P.; Singh, S. K. Synthetic Studies on Arene-Olefin Cycloadditions-VIII. Total Synthesis of (±)-Silphiperfol-6-ene, (±)-7αH-Silphiperfol-5-ene and (±)-7βH-Silphiperfol-5-ene. Tetrahedron Lett. 1985, 26, 5987-5990).
48. Jakupovic, J.; Zdero, C.; Paredes, L.; Bohlmann, F. Sesquiterpene Glycosides and Other Constituents from Osteospermum Species. Phytochemistry 1988, 27, 2881-2886.
49. Knudsen, M. J.; Shore, N. E. Synthesis of the Angularly Fused Triquinane Skeleton via Intramolecular Organometallic Cyclization. J. Org. Chem. 1984, 49, 5025-5026.
50. Huguet, J.; Karpf, M.; Dreiding, A. S. Synthesis of a Stereoisomer of Ptychanolide. Tetrahedron Lett. 1983, 24, 4177-4180.
51. Still, W. C.; Kahn, M.; Mitra, A. Rapid Chromatographic Technique for Preparative Separations with Moderate Resolution. J. Org. Chem. 1978, 43, 2923-2925.
52. Kofron, W. G.; Baclawski, L. M. A Convenient method for Estimation of Alkyllithium Concentrations. J. Org. Chem. 1976, 41, 1879-1880.
53. 3 Synth. Complex. Commun. 1981, 11, 139-140.
54. Sigma Chemical Co., S-6628 Silica-Gel for Thin Layer Chromatography, Type H, Size 10-40 μ, binder: none.