Anthracyclinones. Enantioselective synthesis of 9-alkyanthracyclinone via highly diastereocontrolled alkylation of 4-cyanofuranosugars

Abstract

An efficient method for the enantio- and diastereo-controlled construction of potentially tertiary alcohol by alkylation of an α-cyano-carbanion derived from 1,2-O-isopropylidene-3-deoxy-β-L-threo-pentofuranuronitrile 6 as chiral template has been developed; the method has been applied to the stereocontrolled synthesis of optically active 4-demethoxy feudomycinone C 4.