Synthesis of (±)-Bisavenanthramide B-6 by an Anionic Anhydride Mannich Reaction

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• 作者：Michael J. Di Maso ; Gabriella M. Nepomuceno ; Michael A. St. Peter ; Haley H. Gitre ; Kevin S. Martin ; Jared T. Shaw
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：April 15, 2016
• 年：2016
• 卷：18
• 期：8
• 页码：1740-1743
• 全文大小：357K
• 年卷期：0
• ISSN：1523-7052

文摘

Bisavenanthramide B-6 (2) is a highly substituted γ-lactam derived from oat leaves. Development of a new base-promoted anhydride Mannich reaction with N-sulfonylated imines that forms the core structure of 2 in a single step is presented. Further elaboration allows for a facile one-pot double Buchwald N-arylation to install the final rings onto the densely substituted γ-lactam core. This route provides the natural product in a longest linear sequence of nine steps.