Synthesis of dl-Pumiliotoxin C Hydrochloride and Its Crystal Structure

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概要

• 論文の詳細を見る

• Racemate of pumiliotoxin C which is a toxic constituent of skin extracts of Neotropical frogs, Dendrobates pumilio and Dendrobates auratus, was synthesized. The epoxy-lactam (8) was synthesized from octahydroquinolone (4) via the N-benzyl-cis-octahydroquinolone (7). The bromohydrin (9) from 8 was successively subject to Jones' oxidation, dehydrobromination, and the conjugated addition to give the methyl-ketone (14). The thio-lactam (40) was obtained from the methyl-ketone (14) via the decahydroquinolone (39). Using the Eschenmoser's procedure, the thio-lactam (40) was transformed to the vinylogous amide (42). Catalytic hydrogenation of 42,followed by Jones' oxidation, gave the aminoketone (44). Reductive desulfurization of the thioacetal (45) gave dl-pumiliotoxin C (46), the stereochemistry of which was confirmed by a single crystal X-ray analysis. Three stereoisomers, (17), (19), and (36), of the methyl-ketone (14) were also prepared.

• 公益社団法人日本薬学会の論文
• 1975-11-25

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

• 真崎 規夫

  京大薬

• 佐治 幾太郎

  京大・薬

• 犬伏 康夫

  Faculty Of Pharmaceutical Sciences Kyoto University

• 佐治 幾太郎

  Faculty of Pharmaceutical Sciences, Kyoto University

• 真崎 規夫

  阪大理

• 真崎 規夫

  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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