Asymmetric Synthesis of Anthracyclinones : Regio- and Stereoselective Synthesis of (-)-7-Deoxydaunomycinone through Direct Asymmetric Introduction of an Alkynyl Unit into C9 Ketone

概要

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A New chiral AB-building block (5) for preparing optically active anthracyclinones was synthesized via compound 13a, which was obtained by the stereoselective nucleophilic addition of (trimethylsilyl)ethynylmagnesium chloride to the chiral 6-bromo-1-oxo-β-tetralone 1-acetal (12) derived from (-)-(2S, 3S)-1,4-dimethoxy-2,3-butanediol. Synthesis of (-)-7-deoxydaunomycinone [(-)-4] was achieved through a regiospecific condensation of 5 and 4-acetoxy-8-methoxyhomophthalic anhydride (18). The optical purity (100% ee) of (-)-4 was unambiguously confirmed by high performance liquid chromatographic analysis of (±)-4 and (-)-4 on a chiral column and also by proton nuclear magnetic resonance examination of the methylated compounds, (±)- and (-)-21,using the chiral shift reagent, tris[3-(trifruoromethylhydroxymethylene)-d-camphorato]europium(III) [Eu(tfc)_3].
社団法人日本薬学会の論文
1990-07-25