Resolution of an Iridoid Synthon, Gastrolactol, by Means of Dynamic Acetylation and Lipase-Catalyzed Alcoholysis
- 18 July 2001
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 66 (16) , 5384-5387
- https://doi.org/10.1021/jo015592y
Abstract
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.Keywords
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