Concise access toward chiral hydroxy phenylpropanoids: Formal synthesis of Virolongin B; Kigelin; Kurasoin A; 4-Hydroxysattabacin and Actinopolymorphol A

Abstract

A simple, two step strategy consisting of Sharpless asymmetric dihydroxylation followed by regioselective breaking of C-O bond is utilized to target key chiral intermediates of natural products virolongin B, kigelin, kurasoin A, 4-hydroxy-sattabacin and actinopolymorphol A. Derivatives of enantiopure hydroxy phenyl propanoids and ?-hydroxy Weinreb amides are synthesized. The reductive cleavage of C-O bond in a regioselectve manner is obtained using Pd/C in methanol.