New Insights into the Mechanism and an Expanded Scope of the Fe(III)-Mediated Vinblastine Coupling Reaction

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• 作者：Hiroaki Gotoh ; Justin E. Sears ; Albert Eschenmoser ; Dale L. Boger
• 刊名：The Journal of the American Chemical Society
• 出版年：2012
• 出版时间：August 15, 2012
• 年：2012
• 卷：134
• 期：32
• 页码：13240-13243
• 全文大小：374K
• 年卷期：v.134,no.32(August 15, 2012)
• ISSN：1520-5126

文摘

A definition of the scope of aromatic substrates that participate with catharanthine in an Fe(III)-mediated coupling reaction, an examination of the key structural features of catharanthine required for participation in the reaction, and the development of a generalized indole functionalization reaction that bears little structural relationship to catharanthine itself are detailed. In addition to providing insights into the mechanism of the Fe(III)-mediated coupling reaction of catharanthine with vindoline suggesting the reaction conducted in acidic aqueous buffer may be radical mediated, the studies provide new opportunities for the preparation of previously inaccessible vinblastine analogs and define powerful new methodology for the synthesis of indole-containing natural and unnatural products.