Experiments Directed Towards the Synthesis of Anthracyclinones. XXVI. The Preparation of Chiral Intermediates for Anthracyclinone Synthesis

Abstract

(2′R)-1,5-Dimethoxy-2(2′-methyloxiran-2′-ylmethyl) anthraquinone (8), an intermediate for the synthesis of fridamycin E, has been prepared enantioselectively via the diol (15). The diol (15) was prepared in high yield by asymmetric cis-hydroxylation of the alkene (11). The analogous diol (22), a vineomycinone B₂ precursor, was also prepared.