Stereochemical Studies. XXXIX. A Novel Method for the Preparation of Optically Active Aldehydes. Syntheses of Optically Active (R) (+)-α-Cyclocitral, (S) (+)-Dehydrovomifoliol, and (S) (+)-Abscisic Acid

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概要

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• It was found that direct hydrolysis of the crude oxazolidine derivatives (3a, b), prepared with dl-α-cyclocitral (dl-1a), or its 6-benzoxy derivative (dl-1b) and (S) (+)-prolinol ((S) (+)-4), with aqueous acetic acid, afforded (R) (+)-1a, 19% optically pure, and (S) (+)-6-hydroxy-α-cyclocitral ((S) (+)-2b), 63% optically pure, respectively. A merit of the resolution method is that optically active (R) (+)-1a or (S) (+)-2b can be obtained without any recrystallizations. Some mechanistic studies and discussions on the hydrolysis were also examined. Optically active (S) (+)-2b, thus obtained, was successfully converted into (S) (+)-dehydrovomifoliol ((S) (+)-5) via (S) (+)-6-hydroxy-α-ionone ((S) (+)-9). By this chemical conversion, (S) (+)-abscisic acid could be formally synthesized from dl-1b.

• 公益社団法人日本薬学会の論文
• 1976-02-25

著者

• 柴崎 正勝

  東大院薬

• 柴崎 正勝

  Faculty Of Pharmaceutical Sciences Teikyo University:(present Address)faculty Of Pharmacertical Scie

• 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

• 柴崎 正勝

  Faculty Of Pharmaceutical Sciences Hokkaido University

• 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

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