24 リコポジウム塩基Serratinineの全合成

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概要

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• Serratinine (1), an alkaloid from Lycopodium species, has been synthesized. The Diels-Alder reaction of (9) derived from (11), with butadiene gave the compound (10), which was successively treated with Zn-AcOH, NaBH_4, AC_2O-Py., and OSO_4-NaClO_3 to afford the alcohols (18), (19), and (20). Hydrogenation of the acetonide of (18), followed by acid hydrolysis gave the compound (22). The compound (22) was also obtained from (19). Oxidation of (22) with HIO_4 provided the dialdehyde (24). Treatment of (24) with basic alumina or with a trace of piperidine acetate in dry benzene gave only the compound (25), whereas treatment of (24) with excess pyrrolidine acetate in dry MeOH afforded selectively the compound (26). The Wittig reaction of (26) gave the compound (35) which was hydrogenated over (φ_3P)_3RhCl to afford (36). Reduction of (36) with CoCl_2-NaBH_4 yielded the compound (37) which was treated with NCS and Cu_2Cl_2 to give the aziridines (38) and (39) in 20 and 3%, respectively. Reduction of (38) with LiBH_4 provided the alcohol (40), which on treatment with TsCl-Pyridine gave the quaternary base (41). When refluxed with AcOK in EtOH, the compound (41) gave the triacetate (42), and hydrolysis of (42), followed by oxidation with Jones'reagent afforded the triketone (45). Finally, reduction of (45) with NaBH_4 gave dl-serratinine (46) and dl-8-episerratinine (47).

• 天然有機化合物討論会の論文
• 1974-10-01

著者

• 原山 尚

  Faculty Of Pharmaceutical Sciences Kyoto University

• 犬伏 康夫

  京大薬学科

• 原山 尚

  京大薬

• 沖 正信

  Faculty Of Pharmaceutical Sciences Kyoto University

• 大谷 光昭

  Shionogi Research Laboratories Shionogi & Co. Ltd.

• 大谷 光昭

  京大薬

• 沖 正信

  京大薬

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