Enantioselective synthesis of both (+)-and (-)-derivatives of bicyclo[4.3.0]nonan-8-one and -3,8-diones from R-carvone 1

Tetrahedron Letters

Volumn 37, Issue 10, 1996, Pages 1679-1682

  Srikrishna, Adusumilli ^a   Reddy, T Jagadeeswar ^a   Nagaraju, Sankuratri ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

INDENE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029875974     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00106-2     Document Type: Article

References (15)

1. Chiral synthons from carvone Part 16. For part 15, see Srikrishna, A.; Nagaraju, S.; Reddy, T.J.; Venkateswarlu, S. Pure and Appl. Chem., in press.
2. Heathcock, C.H.; Graham, S.L.; Pirrung, M.C.; Plavac, F.; White, C.T. The total synthesis of sesquiterpenes, Ed.J. ApSimon, John Wiley & Sons, New York, 1983.
3. Srikrishna, A.; Krishnan, K. J. Org. Chem., 1993, 58, 7751; Srikrishna, A.; Nagaraju, S.; Venkateswarlu, S. Tetrahedron Lett., 1994, 35, 429.
4. Srikrishna, A.; Krishnan, K. J. Org. Chem., 1993, 58, 7751; Srikrishna, A.; Nagaraju, S.; Venkateswarlu, S. Tetrahedron Lett., 1994, 35, 429.
5. Ho, T.-L. Enantioselective synthesis, natural products from chiral terpenes, John Wiley & Sons, Inc.; New York, 1992.
6. Swarts, H.J.; Verstegen-Haaksma, A.A.; Jansen, B.J.M.; de Groot, A. Tetrahedron, 1994, 50, 10083 and references cited therein. For other synthesis of decalins from carvone see, Gesson, J.-P.; Jacquesy, J.-C.; Renoux, B. Tetrahedron, 1989, 45, 5853.
7. Swarts, H.J.; Verstegen-Haaksma, A.A.; Jansen, B.J.M.; de Groot, A. Tetrahedron, 1994, 50, 10083 and references cited therein. For other synthesis of decalins from carvone see, Gesson, J.-P.; Jacquesy, J.-C.; Renoux, B. Tetrahedron, 1989, 45, 5853.
8. Srikrishna, A.; Reddy, T.J. Indian J. Chem., 1995, 34B, 844.
9. Garver, L.; van Eikeren, P.; Byrd, J.E. J. Org. Chem., 1976, 41, 2773.
10. 2), 48.1 (t, C-9), 44.8 (t, C-7), 40.5 (s, C-1), 38.6 (d), 37.1 (d), 34.6 (t), 33.8 (2C, d & t), 25.8 (q), 21.0 (q), 16.0 (q).
11. Okamura, W.H.; Aurrecoechea, J.M.; Gibbs, R.A.; Norman, A.W. J. Org. Chem., 1989, 54, 4072.
12. We have not observed any improvement in the ratio at low temperature.
13. For a similar result, see, Bernasconi, B.; Ferrari, M.; Gariboldi, P.; Jommi, G.; Sisti, M. J. Chem. Soc., Perkin Trans. 1, 1981, 1994.
14. Tsuji, J.; Shimizu, I.; Yamamoto, K. Tetrahedron Lett., 1976, 2975.
15. Thomas, A.F.; Ozainne, M.; Guntz-Dubini, R. Can. J. Chem., 1980, 58, 1810.