Studies on New Synthetic Pathways to ⊿^<α, β>-butenolides from α-Methylbutanolides. III. Regiospecific Preparation of α-Methyl-⊿^<α, β>-butenolides and α-Methylene-γ-butyrolactones by Electrolysis of α-Carboxy-α-methylbutanolides and by Oxidat

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概要

• 論文の詳細を見る

• New methods have been developed for the preparation of α-methylene-γ-butyrolactones (exo-type olefin) and α-methyl-⊿^<α, β>-butenolides (endo-type olefin) starting from an α-carboxy-α-methyl-γ-butyrolactone in a fused lactone system, e. g., (+)-11β-carboxy-(2a) and (+)-11α-carboxy-3α, 4β, 5α, 6βH-hexahydrosantonin (2c). The method for exocyclic (⊿^<α, β'>) butenolides, e. g., ⊿^<11(13)>-dehydrohexahydrosantonin (5a), consists of the oxidative syn elimination of an 11β-oriented α-dimethylaminolactone (4b) derived smoothly with retention of the configuration of the α-substituent through several intermediates, starting from an α-carboxy-α-methylbutanolide, e. g., 11β-carboxy-3α, 4β, 5α, 6βH-hexahydrosantonin (2a) (11β-COOH/7α-H : trans). The method for endo-type butenolides, e. g., ⊿^<7(11)>-dehydrohexahydrosantonin (8a), consists of electrolytic oxidation of the trans- or cis-carboxylactone acid, e. g., 11β-carboxy-(2a) and 11α-carboxy-3α, 4β, 5α, 6βH-hexahydrosantonin (2c) (11α-COOH/7α-H : cis), irrespective of the configuration of the α-carboxyl group in the santanolide.

• 公益社団法人日本薬学会の論文
• 1980-01-25

著者

• 稲山 誠一

  Pharmaceutical Institute, School of Medicine, Keio University

• 川又 健

  Pharmaceutical Institute, School of Medicine, Keio University

• 清水 信子

  Pharmaceutical Institute, School of Medicine, Keio University

• 稲山 誠一

  Institute Of Oriental Medical Sciences

• 稲山 誠一

  Pharmaceutical Institute School Of Medicine Keio University

• 稲山 誠一

  慶應義塾大学医学部薬化学研究所

• 清水 信子

  Pharmaceutical Institute School Of Medicine Keio University

• 川又 健

  Pharmaceutical Institute School Of Medicine Keio University

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