Synthesis of the N-((1E)-alkenyl)-(2Z,4Z)-heptadienamide side chain of salicylihalamide A and apicularens A and B

Abstract

(matrix presented) The unstable N-((1E)-alkenyl)-(2Z,4Z)-heptadienamide side chain of salicylihalamide A (1) and apicularens A and B (3 and 4) has been prepared in one pot by the addition of (1Z,3Z)-hexadienylcuprate, prepared in situ from EtLi, CuBr-SMe2, and acetylene, to a (1E)-alkenyl isocyanate.