Tetrahedron

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

文献索引：Martelli, J.; Gree, D.; Kessabi, J.; Gree, R.; Toupet, L. Tetrahedron, 1989 , vol. 45, # 13 p. 4213 - 4226

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被引用次数: 7

摘要

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 ...