Stereochemical Studies. XXXIV. A Novel Biogenetic-type Cyclization of Citral to α-Cyclocitral via an Enamine

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概要

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• Aminig to develop a new biogenetic-type cyclization of acyclic terpene derivatives which is applicable to the asymmetric synthesis of optically active terpenes, a novel acidcatalyzed cyclization of the dienamines (7) easily prepared with citral (1) and several kinds of secondary amines, was studied. Treatment of citral-pyrrolidine enamine (7a) with a mixture of concd. sulfuric acid and water, followed by hydrolysis, was found to exclusively afford α-cyclocitral (2) in 41% yield. Detailed studies on the structure of 7 and the reaction mechanism for the new cyclization reaction were also carried out.

• 公益社団法人日本薬学会の論文
• 1975-02-25

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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