Anthracyclines. XIII The Synthesis of (+)-(4R,6R)- and (+)-(4S,6R)-6-Acetyl-6-(t-butyldimethylsilyloxy)-4-ethoxy-4-methoxy-5,6,7,8-tetrahydronaphthalen-1(4H)-one: New Chiral AB Synthons for the Synthesis of (—)-7-Deoxydaunomycinone

Abstract

The title dienones have been prepared from (-)-(2R,1′S)-8-benzyloxy-2-(1′-hydroxyethyl)-5-methoxy-1,2,3,4-tetrahydronaphthalen-2-ol, by a series of reactions in which the selective cleavage of an aryl methyl ether in the presence of an aryl ethyl ether plays a key role. This 10- step sequence proceeds in an overall yield of 55%, and chiral integrity is preserved throughout.