Concise Assembly of the Polycyclic Frameworks Associated with the Hapalindole and Fischerindole Alkaloids

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• 作者：Martin G. Banwell ; Xinghua Ma ; Rebecca M. Taylor ; Anthony C. Willis
• 刊名：Organic Letters
• 出版年：2006
• 出版时间：October 12, 2006
• 年：2006
• 卷：8
• 期：21
• 页码：4959 - 4961
• 全文大小：67K
• 年卷期：v.8,no.21(October 12, 2006)
• ISSN：1523-7052

文摘

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Reaction of N-methylindole (4) with 6,6-dibromobicyclo[3.1.0]hexane (5) in the presence of silver tetrafluoroborate affords conjugate 7 in 67%yield. This product can be readily elaborated to compounds 12b and 13b which embody the polycyclic frameworks associated with membersof the hapalindole and fischerindole classes of alkaloids. The chiral-auxiliary-substituted 6,6-dibromobicyclo[3.1.0]hexanes 21 and 22 reactwith indole to give adducts likely to be useful in the enantioselective total synthesis of the title alkaloids.