Total Synthesis of the Alkaloid (±)-Metaphanine

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概要

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• (±)-Metaphanine (49), which is a member of hasubanan alkaloids and possesses an intramolecular hemiketal ring, was synthesized. The keto-lactam (5)^<3)> was derived to the diacetoxy-ketal (13) via the O-acetyl-ketolactam (11). The compound (13) was oxidized to the 10-oxo compound (16) which was reduced stereoselectively to the trans diol-lactam (22), a C_<10>-hydroxy group of which was selectively protected by an acetyl group or by a tetrahydropyranyl group to give the trans 10-acetoxy compound (23) or the monotetrahydropyranyl ether (33), both of which were oxidized and hydrolyzed to provide (±)-7-ethyleneketal-16-oxo-metaphanine (36). The selective reduction of the lactam carbonyl group of the compound (36) by the Borch's method^<4)> gave (±)-7-ethyleneketal-metaphanine (44) which was hydrolyzed to give (±)-metaphanine (49).

• 公益社団法人日本薬学会の論文
• 1974-04-25

著者

• 犬伏 康夫

  Faculty of Pharmaceutical Sciences, Kyoto University

• 井深 俊郎

  Faculty of Pharmaceutical Sciences, Kyoto University

• 田中 圭

  Faculty Of Pharmaceutical Sciences Kyoto University

• 田中 圭

  静岡県大 薬

• 井深 俊郎

  Faculty Of Pharmaceutical Sciences Kyoto University

• 犬伏 康夫

  Faculty Of Pharmaceutical Sciences Kyoto University

• 田中 圭

  京都大学薬学部

• 田中 圭

  Faculty of Eng., Oita Univ.

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