Single-step synthesis of cyclopentenones from (3-alkoxycarbonyl-2-oxo-propylidene)triphenylphosphorane and 1,2-diacylethylenes

Tetrahedron Letters

Volumn 37, Issue 3, 1996, Pages 401-404

  Hatanaka, Minoru ^a   Ishida, Akiharu ^a   Tanaka, Yasuhiro ^a   Ueda, Ikuo ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTENONE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030071594     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02186-8     Document Type: Article

References (14)

1. For excellent reviews, see: Ramaiah, M. Synthesis, 1984, 529. Little, R. D. Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I., Eds., Pergamon, Oxford, 1991, Vol. 5, 239. Habermas, K. L.; Denmark, S. E. Org. Read. 1994, 45, 1.
2. For excellent reviews, see: Ramaiah, M. Synthesis, 1984, 529. Little, R. D. Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I., Eds., Pergamon, Oxford, 1991, Vol. 5, 239. Habermas, K. L.; Denmark, S. E. Org. Read. 1994, 45, 1.
3. For excellent reviews, see: Ramaiah, M. Synthesis, 1984, 529. Little, R. D. Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I., Eds., Pergamon, Oxford, 1991, Vol. 5, 239. Habermas, K. L.; Denmark, S. E. Org. Read. 1994, 45, 1.
4. Hatanaka, M.; Himeda, Y.; Ueda, I. J. Chem. Soc., Perkin Trans. 1, 1993, 2269; Hatanaka, M.; Himeda, Y.; Imashiro, R.; Tanaka, Y.; Ueda, I. J. Org. Chem. 1994, 59, 111; Hatanaka, M.; Himeda, Y.; Tanaka, Y.; Ueda, I. Tetrahedron Lett., 1995, 36, 3211.
5. Hatanaka, M.; Himeda, Y.; Ueda, I. J. Chem. Soc., Perkin Trans. 1, 1993, 2269; Hatanaka, M.; Himeda, Y.; Imashiro, R.; Tanaka, Y.; Ueda, I. J. Org. Chem. 1994, 59, 111; Hatanaka, M.; Himeda, Y.; Tanaka, Y.; Ueda, I. Tetrahedron Lett., 1995, 36, 3211.
6. Hatanaka, M.; Himeda, Y.; Ueda, I. J. Chem. Soc., Perkin Trans. 1, 1993, 2269; Hatanaka, M.; Himeda, Y.; Imashiro, R.; Tanaka, Y.; Ueda, I. J. Org. Chem. 1994, 59, 111; Hatanaka, M.; Himeda, Y.; Tanaka, Y.; Ueda, I. Tetrahedron Lett., 1995, 36, 3211.
7. Hatanaka, M.; Tanaka, Y.; Ueda, I. Tetrahedron Lett., 1995, 36, 3719.
8. -1.
9. 4, implying the generation of reactive species. The detail will be discussed in a full paper.
10. Pietrusiewicz, K. M.; Monkiewicz, J.; Bodalski, R. J. Org. Chem. 1983, 48, 788. Pietrusiewicz, K. M.; Salammonczyk, I. J. Org. Chem. 1988, 53, 2837.
11. Pietrusiewicz, K. M.; Monkiewicz, J.; Bodalski, R. J. Org. Chem. 1983, 48, 788. Pietrusiewicz, K. M.; Salammonczyk, I. J. Org. Chem. 1988, 53, 2837.
12. Fleming, I. Frontier Orbitals and Organic Chemical Reactions, John Wiley & Sons, Ltd., London, 1976.
13. Barluenga, J.; Baragana, B.; Alonso, A.; Concellon, J. M. J. Chem. Soc., Chem. Commun. 1994, 969.
14. In order to determine the stereochemistry of the major product, the cyclopentenone dimethyl ester 14 (de. 91%) was prepared in a similar manner from the corresponding dimethyl ester of 10b. Compound 14 was converted via the following sequences into the cyclopentenone 15 which showed identical physical data with these reported previously; Klunder, A. J. H.; Huizinga, W. B.; Sessink, P. J. M.; Zwanenburg, B. Tetrahedron Lett., 1987, 28, 357. (equation presented)