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

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

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

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Citation Number: 14

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.

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