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

Document created by Martin Tabor on Aug 22, 2014
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  Org. Lett., 2009, 11 (23), pp 5382–5385


  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.

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