A short synthesis of the tricarbocyclic framework of oreodaphnenol

Tetrahedron Letters

Volumn 39, Issue 16, 1998, Pages 2411-2412

  Sarkar, Tarun K ^a   Nandy, Sandip K ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

OREODAPHNENOL; SESQUITERPENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; STEREOCHEMISTRY; SYNTHESIS; TREE;

EID: 0032537167     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00212-3     Document Type: Article

References (15)

1. 1) Weyerstahl, P.; Marschall-Weyerstahl, H.; Wahlburg, H-C. Liebigs Ann. Chem. 1989, 307.
2. 2) Sarkar, T.K.; Ghorai, B.K.; Nandy, S.K.; Mukharjee, B.; Banerji, A. J. Org. Chem. 1997, 62, 6006 and references cited therein.
3. 3) Private communication from Prof. P. Weyerstahl.
4. 2 was removed by fluoride induced O-Si bond cleavage, seperation of the corresponding alcohols and resilylation.
5. 5) For a review see: McKervey, M.A.; Ye, T. Chem. Rev. 1994, 94, 1091.
6. 6) 6 was prepared from 2 as described for 7.
7. 7) Srikrishna, A.; Krishnan, K. J. Chem. Soc. Parkin Trans. 1 1993, 667.
8. 8) Corey, E. J.; Myers, A. Tetrahedron Lett. 1984, 25, 3559.
9. 9) Taber, D. F.; Hoerrner, R. S. J. Org. Chem. 1992, 57, 441.
10. See also ref. 5.
11. 1H-NMR shows the presence of a trace (∼3%) of the other diastereomer, e.g., 9.
12. 11) For a review see: Hoffmann, R. W. Chem. Rev. 1989, 89, 1841.
13. 12) For a review see: Kane, V. V.; Singh, V.; Martin, A.; Doyle, D. L. Tetrahedron 1983, 39, 345.
14. 13) Frick, U.; Simchen, G. Synthesis 1984, 929.
15. 14) Trost, B.M.; Curan, D.P. J. Am. Chem. Soc. 1989, 102, 5699.