Resolution of an iridoid synthon, gastrolactol, by means of dynamic acetylation and lipase-catalyzed alcoholysis

…, D Rotticci, I Liblikas, T Norin, CR Unelius

文献索引：Santangelo; Rotticci; Liblikas; Norin; Unelius Journal of Organic Chemistry, 2001 , vol. 66, # 16 p. 5384 - 5387

全文：HTML全文

被引用次数: 14

摘要

A short synthetic route to asymmetric iridoids was developed. The three key steps were an intramolecular [4+ 2] cycloaddition reaction of an enamine derivative of 8-oxocitral (2), a dynamic acetylation, and an enzymatic resolution of the gastrolactyl acetates 5a and 5b, iridoids with three stereocenters. Some regio-and stereoselective heterogeneous catalytic hydrogenations of double bonds in iridoid aglucones were discussed.