Epoxycaulerpenynes: Reactivity, and diastereoselective and highly regioselective synthesis by dimethyldioxirane oxidation of caulerpenyne

European Journal of Organic Chemistry

Volumn , Issue 8, 1999, Pages 1985-1990

  Guerriero, Antonio ^a   D'Ambrosio, Michele ^a  

^a UNIVERSITY OF TRENTO   (Italy)

Author keywords

Caulerpa taxifolia; Chemoselectivity; Epoxidation; Natural products; Regioselectivity

Indexed keywords

6,7 EPOXYCAULERPENYNE; CAULERPENYNE; SESQUITERPENE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; EPOXIDATION; NONHUMAN; REACTION ANALYSIS; SEAWEED; STEREOCHEMISTRY; STEREOISOMERISM;

EID: 0032791154     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(199908)1999:8<1985::aid-ejoc1985>3.0.co;2-o     Document Type: Article

References (18)

1. A. Meinesz, B. Hesse, Oceanologica Acta 1991, 14, 415-426.
2. M. A. Ribera, E. Ballesteros, C. F. Boudouresque, A. Gomez, V. Gravez (Eds.), Second International Workshop on Caulerpa taxifolia, Univ. Barcelona Publ., Spain, 1996.
3. V. Amico, G. Oriente, M. Piattelli, C. Tringalli, E. Fattorusso, S. Magno, L. Mayol, Tetrahedron Lett. 1978, 38, 3593-3596.
4. [4a] A. Guerriero, A. Meinesz, M. D'Ambrosio, F. Pietra, Helv. Chim. Acta 1992, 75, 689-695.
5. [4b] A. Guerriero, F. Marchetti, M. D'Ambrosio, S. Senesi, F. Dini, F. Pietra, Helv. Chim. Acta 1993, 76, 855-864.
6. A. Guerriero, D. Depentori, M. D'Ambrosio, M. Durante, F. Dini, C. Geroni, F. Pietra in Second International Workshop on Caulerpa taxifolia (Eds.: M. A. Ribera, E. Ballesteros, C. F. Boudouresque, A. Gomez, V. Gravez), Univ. Barcelona Publ., Spain, 1996, pp. 233-246.
7. A. Guerriero, D. Depentori, M. D'Ambrosio, M. Durante, F. Dini, F. Pietra, J. Chem. Soc., Chem. Commun. 1994, 2083-2084.
8. A. Guerriero, D. Depentori, M. D'Ambrosio, F. Pietra, Helv. Chim. Acta 1995, 78, 1755-1762.
9. [8a] R. Curci, A. Dinoi, M. F. Rubino, Pure Appl. Chem. 1995, 67, 811-822.
10. [8b] R. W. Murray, Chem. Rev. 1989, 89, 1187-1201.
11. [8c] W. Adam, J. Bialas, L. Hadjiarapoglou, Chem. Ber. 1991, 124, 2377.
12. R. W. Murray, D. Gu, J. Chem. Soc., Perkin Trans. 2 1993, 2203-2207.
13. PC MODEL for Windows, Serena Software, Bloomington, IN, 1993.
14. [11a] J. A. Dale, H. S. Mosher, J. Am. Chem. Soc. 1973, 95, 512-515.
15. [11b] I. Ohtani, T. Kusumi, Y. Kashman, H. Kakisawa, J. Am. Chem. Soc. 1991, 113, 4092-409.
16. J. March in Advanced Organic Chemistry, 4th ed., John Wiley & Sons, 1992, p. 248-272.
17. J. R. Schauder, A. Krief, Tetrahedron Lett. 1982, 23, 4389-4392.
18. W. Adam, D. Reinhardt, H.-U. Reissig, K. Paulini, Tetrahedron 1995, 51, 12257-12262.