26 ホモエリスリナアルカロイド,(±)schelhammericine,(±)3-epischelhammericineの全合成

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概要

• 論文の詳細を見る

• This stereo-controlled synthesis of the title alkaloids provides the first total synthesis of the naturally occurring homoerythrinan alkaloids. The key step of our synthesis of the homoerythrinan ring system lies in [2+2]. photocycloaddition of a benzaepino-pyrrolinedione to an activated butadiene followed by the anionic 1,3-rearrangement of the resulting vinyl-oxy-cyclobutane. Starting from safrole, the 2,8-dioxo-Δ^<1(6)>-homoerythrinan derivative 45 was synthesized in 22 steps through the cyclohomo-erythrinan derivative 35 utilizing the above 1,3-anionic rearrangement, 1,2-carbonyl transposition via phenylselenenylation and decarbomethoxylation reaction by group IIa metal halide-DMSO. The compound 45 was stereoselectively reduced to 3β-alcohol 48 by Bu_4NBH_4 and to 3α-alcohol 49 by NaBH_4-CeCl_3. Methylation and AlH_3 reduction of 50 gave (±)-schelhammericine 1. Similarly methylation and reduction of 51 gave (±)-epischelhammericine 2.

• 天然有機化合物討論会の論文
• 1985-09-07

著者

• 津田 喜典

  金沢大学

• 細井 深造

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 細井 深造

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 津田 喜典

  金沢大学薬学部

• 木内 文之

  金沢大薬

• 津田 喜典

  金沢大薬

• 佐野 武弘

  昭和薬大

• 戸田 潤

  Showa College of Pharmaceutical Sciences

• 大島 武

  Faculty Of Pharmaceutical Sciences

• 細井 深造

  金沢大薬

• 大島 武

  金沢大薬

• 金内 総美

  金沢大薬

• 村田 雅美

  金沢大薬

• 戸田 潤

  昭和薬大

• 佐野 武弘

  Showa Pharmaceutical Univ. Tokyo Jpn

• 村田 雅美

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 村田 雅美

  Faculty Of Pharmaceutical Sciences Kanazawa University

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