59 多環系インドールアルカロイドの合成研究 : 2,3のaspidosperma系アルカロイドの全合成並びに二量体型アルカロイド合成の試み

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概要

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• In the series of these studies on the syntheses of poly-cyclic indole alkaloids, the following aspidosperma alkaloids were synthesized from a common intermediate(1). (i) (±)-Fendleridine[=aspidoalbidine(6a)] (Aspidoalbine type) (ii) (±)-Aspidofractinine(14) (Refractine type) (iii) (±)-Deoxyaspidodispermine(20) (Aspidodispermine type) On the other hand, the modified Polonovski reaction of catharanthine(21) with vindoline was developed by Potier et. al., to give the dimeric indole derivative involving the natural configuration at C-18. Thus, for the synthesis of vinblastine or vincristine which are well known to be anticancer agents, an oxygen functional group should be introduced to the double bond of catharanthine in the correct form. In line with this principle, catharanthine was oxidized with Hg(OAc)_2 to give the lactam(22), whose acid was subjected to the iodolactonization, followed by reduction with (n-Bu)_3SnH. The compound (28) was further reduced with BH_3 to furnish the lactone(29), which was hydrolyzed to the corresponding hydroxy acid. However, this hydroxy acid was treated with diazomethane to immediately afford the initial lactone instead of the hydroxy ester. As the reaction condition have not thoroughly examined, the hydroxy ester(30) might be obtained under strict reaction condition. Thus, the dimerization of the lactone(29) with vindoline was attempted, the results of which will be discussed.

• 天然有機化合物討論会の論文
• 1976-09-20

著者

• 伴 義雄

  北大・薬

• 伴 義雄

  東邦大・薬

• 伴 義雄

  Faculty Of Pharmaceutical Sciences Hokkaido University

• 本間 靖

  北大・薬

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