Total Synthesis of (+)-Crocacin C

The total synthesis of (+)-crocacin C is described. The convergent asymmetric synthesis relies on the use of a regio- and diastereoselective epoxidation of an allylic alcohol with m-CPBA followed by epoxide opening with Me(2)CuCNLi(2) and a Stille cross-coupling between E-vinyl stannane 5 and E-vinyl iodide 6 to establish the (E,E)-dienamide moiety. [structure: see text]