Total Synthesis of (-)-Himgaline

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• 作者：Unmesh Shah ; Samuel Chackalamannil ; Ashit K. Ganguly ; Mariappan Chelliah ; Sergei Kolotuchin ; Alexei Buevich ; Andrew McPhail
• 刊名：Journal of the American Chemical Society
• 出版年：2006
• 出版时间：October 4, 2006
• 年：2006
• 卷：128
• 期：39
• 页码：12654 - 12655
• 全文大小：86K
• 年卷期：v.128,no.39(October 4, 2006)
• ISSN：1520-5126

文摘

The first total synthesis of (-)-himgaline and a highly enantioselective synthesis of its congener (-)-GB 13 are described. Decarboxylative aza-Michael reaction of the hexacyclic lactone precursor under acidic conditions, followed by basic workup, yielded (-)-GB 13 in 80% yield. Cyclization of (-)-GB 13 to oxohimgaline under acidic conditions, followed by internally coordinated sodium triacetoxyborohydride reduction, gave (-)-himgaline as the exclusive product.