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Synlett 2000; 2000(1): 1-12
DOI: 10.1055/s-2000-6430
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Vinyl Isocyanates as Useful Building Blocks for Alkaloid Synthesis

James H. Rigby*
  • *Department of Chemistry, Wayne State University, Detroit, MI 48202-3489, USA; Fax 3 13-5 77-13 77; E-mail: jhr@chem.wayne.edu
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Publication Date:
31 December 2000 (online)

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Vinyl isocyanates are readily available, reactive functionalities that can serve as useful "1,4-dipole" equivalents in a wide-range of cyclization processes. In combination with various electron rich "1,2-dipoles" (i.e. enamines and enolates), they can deliver structurally elaborate six-membered nitrogen heterocycles suitable for conversion into a number of alkaloid targets including benzophenanthridines, phenanthridines as well as pyridone-derived systems. Reactions with "1,1-dipoles" (i.e. alkyl isocyanides and nucleophilic carbenes) afford highly functionalized pyrrolidine-based products that are amenable to further transformation into members of the amaryillidaceae, erythrina and stemona alkaloid families.

isocyanates - cyclization - cycloaddition - pyridones - hydroindolones - isocyanides