Studies toward the synthesis of vinigrol. First construction of the tricyclic ring system

Journal of Organic Chemistry

Volumn 62, Issue 15, 1997, Pages 5062-5068

  Devaux, Jean François ^a   Hanna, Issam ^a   Lallemand, Jean Yves ^a  

^a LABORATOIRE DE SYNTHÈSE ORGANIQUE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL ALCOHOL; DITERPENE; MAGNESIUM CHLORIDE; TRIFLUOROACETIC ACID; UNCLASSIFIED DRUG; VINIGROL;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030739751     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970343o     Document Type: Article

References (36)

1. Uchida, I.; Ando, T.; Fukami, N.; Yoshida, K.; Hashimoto, M.; Tada, T.; Koda, S.; Morimoto, Y. J. Org. Chem. 1987, 52, 5292-5293.
2. (a) Ando, T.; Tsurumi, Y.; Ohata, N.; Ushida, I.; Hoshida, K.; Okuhara, M. J. Antibiot. 1988, 41, 25-30.
3. (b) Ando, T.; Yoshida, K.; Okuhara, M. Ibid. 31-35.
4. Norris, D. B.; Depledge, P.; Jakson, A.P. PCT Int. Appl. WO 91 07,953; Chem. Abstr. 1991, 115, 64776 h.
5. For a review on stereocontrolled construction of complex cyclic ketones via oxy-Cope rearrangements, see: Paquette, L. A. Angew. Chem., Int. Ed. Engl. 1990, 29, 609-626.
6. For our preliminary report see: Devaux, J.-F.; Hanna, I.; Lallemand, J.-Y.; Prangé, T. J. Org. Chem. 1993, 58, 2349-2350.
7. Gerlach, H.; Müller, W. Angew. Chem., Int. Ed. Engl. 1972, 11, 1030-1031. Almqvist, F.; Eklund, L.; Frejd, T. Synth. Commun. 1993, 23, 1499-1505.
8. Gerlach, H.; Müller, W. Angew. Chem., Int. Ed. Engl. 1972, 11, 1030-1031. Almqvist, F.; Eklund, L.; Frejd, T. Synth. Commun. 1993, 23, 1499-1505.
9. Scott, W. J.; Crisp, G. T.; Stille, J. K. J. Am. Chem. Soc. 1984, 106, 4630-4632; Org. Synth. 1990, 68, 116-129.
10. Scott, W. J.; Crisp, G. T.; Stille, J. K. J. Am. Chem. Soc. 1984, 106, 4630-4632; Org. Synth. 1990, 68, 116-129.
11. For a review on the chemistry of vinyl sulfones, see: Simpkins, N. S. Tetrahedron 1990, 46, 6951-6984.
12. The numbering used in this paper refers to the corresponding centers of vinigrol.
13. This ratio (2.5:1 instead 3:1 for 8) is due to further Baeyer-Villiger oxidation of 8a leading to an epoxy lactone.
14. (a) Martin, S. F.; White, J. B.; Wagner, R. J. Org. Chem. 1982, 47, 3190-3192.
15. (b) Paquette, L. A.; Wei, H.; Rogers, R. D. J. Org. Chem. 1989, 54, 2291-2300.
16. The formation of diketone 10 resulted from in situ overoxidation of the enolate formed as a result of the oxy-Cope process. See, for example: Paquette, L. A.; De Russy, N. T.; Pegg, N. A.; Taylor, R. T.; Zydowsky, T. M. J. Org. Chem. 1989, 54, 4576-4581 and references cited therein.
17. Rubottom, G. M.; Gruber, J. M. J. Org. Chem. 1977, 42, 1051-1056.
18. Gemal, A. L.; Luche, J. L. J. Am. Chem. Soc. 1981, 103, 5454-5459.
19. For a similar transformation see: Hung, S. C.; Liao, C. C. Tetrahedron Lett. 1991, 32, 4011-4014.
20. When the reaction was effected at 0°C or below, aromatization occurred, leading to a great amount (30-35%) of undesirable aromatic ketone.
21. Diene 14 must be freed completely of chlorinated byproducts i and ii prior hydrogenation in order to realize reproducibility complete conversion to 15a. (Matrix Presented)
22. 20 (Matrix Presented)
23. For example, see: Morera, E., Ortar, G. J. Org. Chem. 1983, 48, 119-121. Boeckman, R. K.; Springer, D. M.; Alessi, T. R. J. Am. Chem. Soc. 1989, 111, 8284-8286.
24. For example, see: Morera, E., Ortar, G. J. Org. Chem. 1983, 48, 119-121. Boeckman, R. K.; Springer, D. M.; Alessi, T. R. J. Am. Chem. Soc. 1989, 111, 8284-8286.
25. For a related case, see: Brown, W. L.; Fallis, A. G. Can. J. Chem. 1987, 65, 1828-1832.
26. For a review on chelation-controlled reactions, see: Reetz, M. T. Angew. Chem., Int. Ed. Engl. 1984, 23, 556-569.
27. De vaux, J.-F.; Fraisse, P.; Hanna, I.; Lallemand, J.-Y. Tetrahedron Lett. 1995, 36, 9471-9474.
28. For a review, see: Hutchins, O.; Hutchins, M. K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 8, pp 327-362.
29. Treatment of 22 with lithium aluminum hydride in THF at 0 °C was found to give 24 (98%) as the only detectable stereoisomer. Assignment of configuration to this alcohol was deduced from X-ray crystallographic analysis of the acid-catalyzed rearrangement product of its methyl ether, see: Devaux, J.-F.; Hanna, I.; Lallemand, J.-Y.; Prange, T. J. Chem. Res., Synop. 1996, 32. Under the same conditions, ketones 23 and 19 afforded 25 and 30, respectively.
30. Barton, D. H. R.; McCombie, S. W. J. J. Chem. Soc., Perkin Trans. 1 1975, 1574-1585.
31. Ireland, R. E.; Giger, R.; Kamata, S. J. Org. Chem. 1977, 42, 1271-1283.
32. Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277-7287. Ireland, R. E.; Liu, L. J. Org. Chem. 1993, 58, 2899.
33. Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277-7287. Ireland, R. E.; Liu, L. J. Org. Chem. 1993, 58, 2899.
34. Crabtree, S. R.; Alex Chu, W. L.; Mander, L. N. Synlett 1990, 169-170.
35. Kobayashi, S.; Hachiya, I. J. Org. Chem. 1994, 59, 3590-3596.
36. The author has deposited atomic coordinates for 8a and 19 with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.