Etude de la diastéréosélectivité dans les réactions de Diels-Alder intramoléculaires à partir d'alcools diéniques; syntheses courtes de lactones polyfonctionnelles
J Martelli, D Grée, J Kessabi, R Grée, L Toupet
Index: Martelli, J.; Gree, D.; Kessabi, J.; Gree, R.; Toupet, L. Tetrahedron, 1989 , vol. 45, # 13 p. 4213 - 4226
Full Text: HTML
Citation Number: 7
Abstract
The methyl-1 alkyl 5 dienols 6 and 7 react with maleic anhydride to give the intramolecular Diels-Alder adducts 11 to 14. The epoxydation of these unsaturated lactones occurs with a good diastereoselectivity. This short sequence allows an efficient synthesis of polyfunctionnalized lactones bearing seven asymmetric centers. An extension to chiral synthesis appears possible since the starting dienols could be obtained in a chiral form ...
Related Articles:
Palladium??Catalyzed Dienylations of Chelated Enolates
[Basak, Sankar; Kazmaier, Uli European Journal of Organic Chemistry, 2008 , # 24 p. 4169 - 4177]
[Franck, Richard W.; Argade, S.; Subramaniam, C. S.; Frechet, Denise M. Tetrahedron Letters, 1985 , vol. 26, # 27 p. 3187 - 3190]
[Fleischacker; Woods Journal of the American Chemical Society, 1956 , vol. 78, p. 3436,3439]
The mechanism of rearrangement of chorismic acid and related compounds
[Gajewski,J.J.; Jurayj,J.; Kimbrough,D.R. Journal of the American Chemical Society, 1987 , vol. 109, p. 1170]
Intramolecular diels-alder reactions of silyl acetal-tethered trienes
[Ainsworth, Peter J.; Craig, Donald; Reader, John C.; Slawin, Alexandra M. Z.; White, Andrew J. P.; Williams, Dawid J. Tetrahedron, 1995 , vol. 51, # 42 p. 11601 - 11622]