Asymmetric Synthesis of optically Active Anthracyclinone Intermediate and 4-Demethoxyanthracyclinones by the Use of a Novel Chiral Reducing Agent

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概要

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• Asymmetric reduction of 2-acetyl-5,8-dimethoxy-3,4-dihydronaphthalene (1) with a novel modified hydride, originally prepared by partial decomposition of lithium aluminum hydride with (1R, 2S)-(-)-N-methylephedrine (1.0 eq) and N-ethylaniline (2.0 eq), was found to proceed highly stereoselectively, giving (S)-(-)-2-1'-hydroxyethyl-5,8-dimethoxy-3,4-dihydronaphthalene ((S)-(-)-2) in 100% chemical and 92% optical yields. Direct recrystallzation of (S)-(-)-2,92% e.e., afforded optically pure (S)-(-)-2 in 87% yield based on 1. Optically pure (S)-(-)-2 was converted to (R)-(-)-2-acetyl-5,8-dimethoxy-1,2,3,4-tetrahydro-2-naphthol ((R)-(-)-3), 100% e.e., a versatile key intermediate for optically active anthracyclinone synthesis, in a good overall yield according to the reaction scheme established in the preceding paper. Synthesis of optically pure (+)-4-demethoxydaunomycinone ((+)-4d) and (+)-4-demethoxyadramycinone ((+)-4c) was accomplished by using optically pure (R)-(-)-3 as a starting material and by following the reported synthetic scheme with slight modifications.

• 公益社団法人日本薬学会の論文
• 1983-03-25

著者

• 寺島 孜郎

  (財)相模中央化学研究所

• 寺島 孜郎

  Faculty Of Pharmaceutical Sciences University Of Tokyo:(present Address)sagami Chemical Research Cen

• 丹野 紀彦

  Faculty Of Pharmaceutical Sciences University Of Tokyo

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