A comparative study of the synthetic paths from 1-butyne to 2E,4Z-heptadien-1-ol

Article abstract of DOI:10.1007/BF00704017

2E,4Z-Heptadien-1-ol (1), the key intermediate in the synthesis of the grapevine moth sex pheromone, was obtained from 1-butyne by a number of alternative procedures, including various variants of the stereocontrolled building of the conjugated E,Z-diene system (Cadiot-Chodkiewicz cross-coupling, alkyne-vinyl halide cross-coupling catalyzed by palladium complexes, anionotropic allylic rearrangement, partial cis- and trans-reduction of the triple bond).None of them could provide for configurational uniformity of 1.The most acceptable path to obtain 1 in multigram amounts appears to be that which proceeds via the conjugated diynol and enynol intermediates with subsequent catalytic cis-hydrogenation.