Synthesis of Demissidine by a Ring Fragmentation 1,3-Dipolar Cycloaddition Approach

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• 作者：Zhe Zhang ; Geoffrey M. Giampa ; Cristian Draghici ; Qiufeng Huang ; Matthias Brewer
• 刊名：Organic Letters
• 出版年：2013
• 出版时间：May 3, 2013
• 年：2013
• 卷：15
• 期：9
• 页码：2100-2103
• 全文大小：233K
• 年卷期：v.15,no.9(May 3, 2013)
• ISSN：1523-7052

文摘

A synthesis of the steroidal alkaloid demissidine from epiandrosterone is reported. A ring fragmentation reaction that efficiently ruptured the D-ring of a diazo ester derivative of epiandrosterone to provide an aldehyde tethered ynoate product was key to this sequence. Incorporation of the indolizidine framework was achieved by an azomethine ylide 1,3-dipolar cycloaddition.