SYNTHESIS OF BRANCHED-CHAIN HEXULOSE DERIVATIVES AS MODEL FOR THE SYNTHESIS OF TALAROMYCINS

Abstract

The synthesis of 3,5-dideoxy-1,2-O-isopropylidene-5-C-hydroxymethyl-β-D-erythro- (1) and α-L-threo-hexulopyranose (2) from 3-deoxy-1,2-O-isopropylidene-β-D-erythro-hexulopyranose (5) from D-fructose is described, as well as their respective transformation into 3,5-dideoxy-1,2-O-isopropylidene-5-C-hydroxymethyl-β-D-threo-(3) and -α-L-erythro-hexulopyranose (4) by inversion of configuration at C-4.

ACKNOWLEDGMENTS

The authors are deeply grateful to Ministerio de Educación y Cultura (Spain) for finantial support (Project PB98-1357) and for a grant (J. A. Tamayo).