Stereochemical Studies. XLII. Asymmetric Synthesis of naturally Occurring Podocarpic Acid

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概要

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• Optically active methyl deoxypodocarpate ((S) (+)-5b), 92% optically pure, was synthesized from (R) (+)-δ-ketoaldehyde ((R) (-)-3a) which was obtainable by the asymmetric synthesis using D-proline-derived pyrrolidine ((R)-4 (R_2=CH_2NC_4H_3)) as a chiral additive. The chemical scheme which was previously developed, was used for the conversion of (R) (-)-3a to (S) (+)-phenanthrone derivative ((S) (+)-1a), and a combination of reductive carbomethoxylation and reductive alkylation was adopted for preparing (S) (+)-5b from (S) (+)-1a. Since (S) (+)-5b had already been converted to naturally occurring podocarpic acid ((S) (+)-5a), the asymmetric synthesis of (S) (+)-5a was accomplished.

• 公益社団法人日本薬学会の論文
• 1976-06-25

著者

• 山田 俊一

  Faculty of Pharmaceutical Sciences, University of Tokyo

• 山田 俊一

  Faculty Of Pharmaceutical Sciences University Of Tokyo

• 寺島 孜郎

  Faculty of Pharmaceutical Sciences, University of Tokyo

• 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

• 曽根 孝範

  Faculty of Pharmaceutical Sciences, University of Tokyo

• 曽根 孝範

  Life-science Institute, Asahi Chemical Industry Co., Ltd.

• 曽根 孝範

  Life-science Institute Asahi Chemical Industry Co. Ltd.

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