Concise access toward chiral hydroxy phenylpropanoids: formal synthesis of virolongin B; kigelin; kurasoin A; 4-hydroxysattabacin, and actinopolymorphol A

摘要

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 alpha-hydroxy Weinreb amides are synthesized. The reductive cleavage of C-O bond in a regioselective manner is obtained using Pd/C in methanol. (C) 2016 Elsevier Ltd. All rights reserved.