Tetrahedron

Attempted synthesis of 3-hydroxy-2-octadecylindole. Proposed structural revision of previously prepared 3-hydroxy-2-octadecylindole and a proposed structure of …

RW Clawson, CA Dacko, RE Deavers, NG Akhmedov…

Index: Clawson Jr., Ronald W.; Dacko, Christopher A.; Deavers III, Robert E.; Akhmedov, Novruz G.; Soederberg, Bjoern C.G. Tetrahedron, 2009 , vol. 65, # 43 p. 8786 - 8793

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Citation Number: 12

Abstract

A synthetic route to 3-hydroxy-2-octadecylindole, the putative structure of the novel indole alkaloid fistulosin, starting from 2-nitro-1-iodobenzene was examined. Key steps include formation of a 1-stannylsubstituted 1-methoxy-1-alkene from a Fischer chromium carbene, intermolecular Kosugi–Migita–Stille coupling, and a palladium-catalyzed reductive N- heteroannulation. Demethylation of 3-methoxy-2-octadecylindole, a possible immediate ...