Martin Tabor - Synthesis of (S)-Jamaicamide C Carboxylic Acid

Version 1

      Publication Details (including relevant citation   information):

      Org. Lett., 2009, 11 (23), pp 5382–5385

      Abstract:

      The jamaicamides are natural product sodium channel blockers   derived from the cyanobacterium Lyngbya majuscula. The   carboxylic acid fragment of jamaicamide C contains a methyl   stereocenter and a trisubstituted E chloroolefin.   Herein, we present the nonracemic synthesis of the aliphatic   chain of jamaicamide C. The methyl stereocenter was installed   using Evans’ oxazolidinone methodology, and the trisubstituted   chloroolefin was set by silylstannylation of a triple bond.

      Address (URL): http://dx.doi.org/10.1021/ol9021222