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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

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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How might you modify this synthesis to prepare the 7 Z ,11 Z isomer of gossyplure

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
Transcribed Image Text: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
Transcribed Image Text: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
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