Stereospecific diene synthesis using acetylene carbocupration; preparation of navel orangeworm pheromone and leukotriene analogues
Abstract
Experimental conditions are described for the conversion of lithium dialkylcuprates into the corresponding doubly vinylogous 1Z,3Z-dienylcuprates using acetylene carbocupration. These dienylcuprates have been trapped with a range of electrophiles to form conjugated Z,Z-dienes in a highly stereospecific manner. The application of this methodology to the synthesis of hexadeca-11Z,13Z-dienal, a principle component of navel orangeworm pheromone, and simple leukotriene B4 analogues is also reported.