Total Syntheses of the Lycopodium Alkaloids (±)-Fawcettimine and (±)-8-Deoxyserratinine

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概要

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• Total syntheses of (±)-fawcettimine (1) and (±)-8-deoxyserratinine (3) have been accomplished. Selective hydrogenation of the conjugated nitrile (6) over (Ph_3P)_3RhCl, followed by reduction with LiAlH_4 and treatment of the product with N_3CO_2-tert-Bu yielded the carbamate (8). Successive treatment of 8 with Na-liquid NH_3,the Jones reagent, N-hydroxysuccinimide-DCC, CF_3CO_2H, and n-Bu_3N in CH_3CN afforded the nine-membered lactam (18). Reduction of 18 with LiBH_4 gave the epimeric alcohols, 22 and 23. Both 22 and 23 were converted into the same ketone (28) via the same sequence of reactions ; reduction with LiAlH_4,acylation with (CF_3CO)_2O-pyridine, selective hydrolysis with 0.2N KOH-MeOH, and Jones oxidation. Epoxidation of 28 gave the epimeric epoxides, 29 and 30. The epoxide (29) was successively treated with BF_3・Et_2O, the Jones reagent, H_2-5% Pd/C, and 1N KOH-MeOH to provide (±)-fawcettimine (1). The other epoxide (30) was converted into (±)-8-deoxyserratinine (3) by successive treatments with 1N KOH-MeOH, the Jones reagent, and NaBH_4.

• 社団法人日本薬学会の論文
• 1980-08-25

著者

• 原山 尚

  Faculty of Pharmaceutical Sciences, Chiba University

• 犬伏 康夫

  Faculty of Pharmaceutical Sciences, Kyoto University

• 高谷 宗男

  京都大学薬学部

• 原山 尚

  Faculty Of Pharmaceutical Sciences Kyoto University

• 高谷 宗男

  Faculty of Pharmaceutical Sciences, Kyoto University

• 犬伏 康夫

  Faculty Of Pharmaceutical Sciences Kyoto University

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