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Resolution of an Iridoid Synthon, Gastrolactol, by Means of Dynamic Acetylation and Lipase-Catalyzed Alcoholysis
journal contribution
posted on 2001-07-18, 00:00 authored by Ellen M. Santangelo, Didier Rotticci, Ilme Liblikas, Torbjörn Norin, C. Rikard UneliusA 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.