Concise syntheses of substituted indolizidine alkaloids via cyclization based on α-sulfinyl carbanions: preparation of (±)-indolizidines 167B and 209D, their epimers, and (±)-tashiromi

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• 作者：Manat Pohmakotr ; Saisuree Prateeptongkum ; Soontorn Chooprayoon ; Patoomratana Tuchinda ; Vichai Reutrakul
• 关键词：Cyclization ; α ; -Sulfinyl carbanion ; (± ; )-Tashiromine ; (± ; )-Indolizidine 167B ; (± ; )-Indolizidine 209D
• 刊名：Tetrahedron
• 出版年：2008
• 出版时间：3 March 2008
• 年：2008
• 卷：64
• 期：10
• 页码：2339-2347
• 全文大小：362 K

文摘

(±)-Indolizidines 167B and 209D, their epimers and (±)-tashiromine have been successfully synthesized, starting from simple γ- or α-lactams. The strategy involves the cyclization of α-sulfinyl carbanion onto the carbonyl group of the lactam ring as the key step, leading to the indolizidines containing the phenylsulfinyl group, which are used as precursors for the preparation of the title compounds.