Gossyplure, the sex pheromone of the pink bollworm, is the acetic ester of 7, 11-hexadeca- dien-1-ol. The active pheromone has the Z configuration at the C7-C8 double bond and is a mixture of E,Z isomers at the C11-C12 double bond. Shown here is the Z,E isomer. CCH3 16 (7Z,11E)-7,11-Hexadecadienyl acetate Following is a retrosynthetic analysis for (7Z,11E)-7,11-hexadecadien-1-ol, which then led to a successful synthesis of gossyplure. Me 0-Si--Bu Ме Me Si--Bu Ме Me H- 0-Si--Bu + Br Me HO Br + H H Br HO, OH Br + H H

Gossyplure, the sex pheromone of the pink bollworm, is the acetic ester of 7, 11-hexadeca- dien-1-ol. The active pheromone has the Z configuration at the C7-C8 double bond and is a mixture of E,Z isomers at the C11-C12 double bond. Shown here is the Z,E isomer. CCH3 16 (7Z,11E)-7,11-Hexadecadienyl acetate Following is a retrosynthetic analysis for (7Z,11E)-7,11-hexadecadien-1-ol, which then led to a successful synthesis of gossyplure. Me 0-Si--Bu Ме Me Si--Bu Ме Me H- 0-Si--Bu + Br Me HO Br + H H Br HO, OH Br + H H

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter11: Ethers, Epoxides, And Sulfides

Section: Chapter Questions

Problem 11.38P

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