STEREOSELECTIVE SYNTHESIS OF SYN-1,3-DIOL ACETONIDES BY REDUCTIVE DECYANATION OF CYANOHYDRINS

: syn- l,3-Diol acetonides are produced with >99:1 selectivity by reductive decyanation of the corresponding cyanohydrin acetonides. Cyanohydrin acetonides (4,6-dialkyl-4-cyano-2,2-dimethyl-l,3-dioxanes) are available from 3-hydroxy aldehydes by cyanohydrin formation and alkylation, or directly from 0-hydroxy ketones. The former method is particularly well suited to the convergent synthesis of alternating (1,3,5,) polyol chains which are found in the polyene macrolide antibiotics1. © 1990, American Chemical Society. All rights reserved.