Bridged to fused ring interchange. The total synthesis of (±)-ledol

Tetrahedron Letters

Volumn 37, Issue 7, 1996, Pages 949-952

  Gwaltney II, Stephen L ^a   Shea, Kenneth J ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LEDOL; SESQUITERPENE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030038001     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02336-4     Document Type: Article

References (22)

1. Gijsen, H. J. M.; Wijnberg, J . B . P. A.; Stork, G . A.; de Groot, A. Tetrahedron 1992, 48, 2465.
2. Tkhu, D. K.; Roshohin, V. I.; Malysheva, O. N.; Solov'ev, V. A. Khim. Drev. 1987, 1, 103.
3. (a) Gwaltney II, S. L.; Sakata, S. T.; Shea, K. J. Tetrahedron Lett. 1995, 36, 7177.
4. (b) Gwaltney II, S. L.; Sakata, S. T.; Shea, K. J. manuscript in preparation.
5. (a) Anet, F. A. L. Conformational Analysis; Chiurdoglu, G., Ed.; Academic: New York, 1971.
6. (b) Anet, F. A. L.; Anet, R. Top. Curr. Chem. 1974, 45, 169.
7. (c) Dale, J. Stereochemistry and Conformational Analysis; Verlag Chemie: New York, 1978.
8. (d) Petasis, N. A.; Patane, M. A. Tetrahedron 1992, 48, 5757 and references cited therein.
9. (e) However, numerous examples can be found of stereoselective transformations involving medium-sized rings. See, for example, Still, W. C.; Galynker, I. Tetrahedron 1981, 37, 3981.
10. Cahiez, G.; Alexakis, A.; Normant, J. F. Tetrahedron Lett. 1978, 3013.
11. (a) Westmijze, H.; Kleijn, H.; Meijer, J.; Vermeer, P. Tetrahedron Lett. 1977, 869.
12. (b) Scott, F.; Cahiez, G.; Normant, J. F.; Villieras, J. J. Organometallic Chem. 1978, 144, 13.
13. Zimmer, R. Synthesis 1993, 165 and references cited therein.
14. (a) Jackson, R. W.; Higby, R. G.; Shea, K. J. Tetrahedron Lettt. 1992, 33, 4695.
15. (b) Jackson, R. W.; Higby, R. G.; Gilman, J. W.; Shea, K. J. Tetrahedron Symposium in Print 1992, 48, 7013.
16. As obtained using Monte Carlo conformational searching in Macromodel V4.5 available from the Department of Chemistry, Columbia University, New York, NY 10027.
17. Mehta, G.; Krishnamurthy, N.; Karra, S. R. J. Am. Chem. Soc. 1991, 113, 5765.
18. Ireland, R. E.; Pfister, G. Tetrahedron Lett. 1969, 2145.
19. (a) Seyferth, D.; Burlitch, J. M.; Minasz, R. J.; Yick-Pui Miu, J.; Simmons Jr., H. D.; Treiber, A. J. H.; Dowd, S. R. J. Am. Chem. Soc. 1965, 87, 4259.
20. (b) Marshall, J. A.; Ruth, J. A. J. Org. Chem. 1974, 39, 1971.
21. Rigby, J. H.; Bellemin, A.-R. Synthesis 1989, 188.
22. Sample obtained from Prof. Joannes B. P. A. Wijnberg. See reference 1 for spectral data and leading references on ledol.