Convergent and stereospecific synthesis of complex skipped polyenes and polyunsaturated fatty acids.

ABSTRACT: Skipped polyenes (that is, 1,4-dienes and higher homologues) are stereodefined components of a vast array of biologically important natural products, including polyunsaturated fatty acids. Although widespread in nature, these architectures are generally considered to represent significant barriers to efficient chemical synthesis. Partial reduction of skipped poly-ynes provides a pathway to a subset of such structures, but general chemical methods for the preparation of skipped polyenes that contain varied stereochemistries and substitution patterns are lacking. Here, we describe a metal-promoted reductive cross-coupling reaction between vinylcyclopropanes and alkynes (or vinylsilanes) that provides stereoselective access to a diverse array of skipped polyenes through a process that establi

SUBMITTER: Macklin TK 

PROVIDER: S-EPMC2909609 | biostudies-literature | 2010 Aug

REPOSITORIES: biostudies-literature