کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
5222283 1383449 2009 8 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Attempted synthesis of 3-hydroxy-2-octadecylindole. Proposed structural revision of previously prepared 3-hydroxy-2-octadecylindole and a proposed structure of fistulosin
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
Attempted synthesis of 3-hydroxy-2-octadecylindole. Proposed structural revision of previously prepared 3-hydroxy-2-octadecylindole and a proposed structure of fistulosin
چکیده انگلیسی

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 precursor to 3-hydroxy-2-octadecylindole, was unsuccessful and gave instead methyl 2-(1-oxononadecanyl)aminobenzoate. The structure of the isolated alkaloid was suggested to be 2-(1-oxooctadecanyl)aminobenzoate by comparison of analytical data with a synthetic sample. In addition, oxidation of 2-octadecylindole gave a 2,2′-dimer, a compound identical to previously prepared 3-hydroxy-2-octadecylindole.

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron - Volume 65, Issue 43, 24 October 2009, Pages 8786-8793
نویسندگان
, , , , ,