Total Synthesis of (+)-ent-Cyclizidine: Absolute Configurational Confirmation of Antibiotic M146791

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• 作者：Stephen Hanessian ; Udaykumar Soma ; Ste虂phane Dorich ; Benoi虃t Desche虃nes-Simard
• 刊名：Organic Letters
• 出版年：2011
• 出版时间：March 4, 2011
• 年：2011
• 卷：13
• 期：5
• 页码：1048-1051
• 全文大小：787K
• 年卷期：v.13,no.5(March 4, 2011)
• ISSN：1523-7052

文摘

The first total synthesis of the enantiomer of the indolizidine alkaloid, cyclizidine, was accomplished from readily available d-serine as the starting chiron. The relevant key reactions involve the stereocontrolled construction of the indolizidine ring system with the required functionality and further elaboration to install the cyclopropyl dienyl side chain. With this total synthesis, the absolute configuration of the natural product based on a redetermination of its X-ray structure has been confirmed.