Strategic use of Nickel(0)-Catalyzed Enyne-Epoxide Reductive Coupling towards the Synthesis of (-)-Cyatha-3,12-diene

Tetrahedron 65(16), 3270-3280, DOI: 10.1016/j.tet.2008.11.086

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.