Stereochemical Studies. XL. A Biomimetic Conversion of L-Lysine into optically Active 2-Substituted Piperidines. Syntheses of D- and L-Pipecolic Acid, and (S) (+)-Coniine from L-Lysine

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概要

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• In order to transform an optical integrity of L-lysine (L-5c) into simple piperidine alkaloids in a biomimetic sence, optically active pipecolic acids (D- or L-10c) or their derivatives ((R) - or (S) -11) were chosen as synthetic intermediates. It was found that deamination of L-5c-HC1 with a combination of sodium nitrite and aqueous hydrochloric acid, followed by the treatment with aqueous base, could give D-10c being more than 90% optically active. On the other hand, deamination of L-5c-1/2H_2SO_4 with sodium nitrite-aqueous sulfuric acid, followed by chlorination with thionyl chloride and pyridine and by cyclization with aqueous base, could afford L-10c which was about 80% optically pure. Precise estimation of retention for optical activity was carried out by isolating formed D- or L-10c as their derivatives ((R) (+)-11a, b or (S) (-)-11b). Exploitations for other synthetic routes to L-10c from L-5c were also undertaken. Based on the above-mentioned experimental results, almost optically pure (S) (+)-coniine, one of the simplest piperidine alkaloids, could be prepared from L-5c-HC1 via D-10c and (R) (+)-11a or b.

• 公益社団法人日本薬学会の論文
• 1976-04-25

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

• 明田 耕一

  Faculty of Pharmaceutical Sciences, University of Tokyo

• 明田 耕一

  Faculty Of Pharmaceutical Sciences University Of Tokyo

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