A Stereoselective Synthesis of dl-Pumiliotoxin C

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概要

• 論文の詳細を見る

• dl-Pumiliotoxin C (1) was stereoselectively synthesized via 5β-methyl-cis-decahydroquinoline-2,7-dione (5) which was prepared in two routes. The Diels-Alder reaction of 1,3-bis (trimethylsiloxy)-5-methylcyclohexa-1,3-diene (6) with acrylonitrile gave the cycloadducts (7) from which anti-8-methyl-exo-2-cyanobicyclo [2. 2. 2] oct-5-en-1-ol (2) was obtained in four steps. Treatment of the compound (2) with acid gave the keto-lactam (5). The Diels-Alder reaction of 1,3-bis (trimethylsiloxy)-1,3-butadiene (11) with ethyl crotonate furnished the adduct (12) from which the keto-lactam (5) was obtained via the compound (19) in seven steps. Reduction of the carbonyl group at the C_7 position and introduction of the n-propyl group at the C_2 position of the keto-lactam (5) gave dl-pumiliotoxin C.

• 社団法人日本薬学会の論文
• 1978-08-25

著者

• 犬伏 康夫

  Faculty of Pharmaceutical Sciences, Kyoto University

• 井深 俊郎

  Faculty of Pharmaceutical Sciences, Kyoto University

• 森 裕二

  Faculty Of Pharmaceutical Sciences Kyoto University

• 井深 俊郎

  Faculty Of Pharmaceutical Sciences Kyoto University

• 犬伏 康夫

  Faculty Of Pharmaceutical Sciences Kyoto University

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