TY - JOUR A1 - Russell, RA A1 - Krauss, AS A1 - Irvine, RW A1 - Warrener, RN T1 - Anthracyclines. XII. The preparation of (—)-(7R)-7-Acetyl-7-(t-butyldimethylsilyoxy-1(4H)-one and (+)-(6R)-6-Acetyl-6-(t-butyldimethylsilyloxy)- 4,4-dimethoxy-5,6,7,8-tetrahydronaphthalene-1(4H)-one: an Improved Route to Chiral AB Synthons for 7-Deoxydaunomycinone JF - Australian Journal of Chemistry JO - Aust. J. Chem. Y1 - 1985 VL - 38 IS - 1 SP - 179 EP - 187 KW - UR - https://doi.org/10.1071/CH9850179 N2 - The title dienones (2) and (5) were prepared from the chiral alcohols (7a) and (7b) respectively. These key starting materials were in turn available from the reduction of 3-acetyl-5-benzyloxy-8-methoxy-1,2- dihydronaphthalene (6a) and 3-acetyl-8-benzyloxy-5-methoxy-1,2- dihydronaphthalene (6b) with lithium aluminium hydride modified with (—)-N- methylephedrine and N- ethylaniline . Chiral phase high-pressure liquid chromatography was used to analyse the enantioselectivity of these reductions which were shown to yield variable results depending upon the origin of the reducing agent. ER -