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

• 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.

Nyckelord

aphid sex-pheromone

actinidia-polygama

glucosides

stereochemistry

biosynthesis

iridolactones

chemistry

cultures

cataria

glands

Ecological chemistry

Ekologisk kemi

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