Strategic use of nickel(0)-catalyzed enyne-epoxide reductive coupling toward the synthesis of (−)-cyatha-3,12-diene

Various situations are explored in which the nickel(0)-catalyzed enyne-epoxide reductive coupling was utilized to access key intermediates toward the total synthesis of (−)-cyatha-3,12-diene (1). Enantioenriched 3,5-dien-1-ols with a variety of functionality were obtained in a straightforward manner from easily accessible 1,3-enynes and terminal epoxides.