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Synthesis 2012; 44(11): 1667-1671
DOI: 10.1055/s-0031-1291006
DOI: 10.1055/s-0031-1291006
paper
Oxidative Cyclization Reactions of Tryptamine Utilizing Hypervalent Iodobenzene in Routes for Pyrroloindole Alkaloid Synthesis
Further Information
Publication History
Received: 31 March 2012
Accepted after revision: 10 April 2012
Publication Date:
10 May 2012 (online)
Abstract
Oxidative cyclization of N-acetyltryptamine by using iodobenzene diacetate (PIDA) provided the corresponding 1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-3a-ol derivative, which could be derivatized following appropriate protection of the two amino and tert-hydroxyl groups. The facile one-pot procedure for cyclization and introduction of the oxygen functionality was applied in concise routes for the synthesis of the natural products CPC-1 and debromoflustraminol B.
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