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Stereoselective Synthesis of Homofarnesenes: Establishment of an Efficient Method for the Stereoselective Preparation of Acyclic Tetrasubstituted Olefins.

ABSTRACT: A new method for the stereoselective synthesis of tetrasubstituted olefins is described. ?-Ketophosphonates are alkylated via conventional methods, and a Grignard reagent is used to diastereoselectively add to the carbonyl group of the resulting intermediates. The elimination of hydroxyl phosphonates yielded the desired tetrasubstituted olefins in a stereoselective manner. Thus, homofarnesenes of fire ant trail pheromones have been synthesized efficiently using this strategy.

SUBMITTER: Yin W

PROVIDER: S-EPMC6641643 | biostudies-literature | 2018 Apr

REPOSITORIES: biostudies-literature

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Stereoselective Synthesis of Homofarnesenes: Establishment of an Efficient Method for the Stereoselective Preparation of Acyclic Tetrasubstituted Olefins.

Yin Wenhao W Liang Weihong W Guo Liping L Lei Jiaheng J Qiu Fayang G FG

ACS omega 20180426 4

A new method for the stereoselective synthesis of tetrasubstituted olefins is described. β-Ketophosphonates are alkylated via conventional methods, and a Grignard reagent is used to diastereoselectively add to the carbonyl group of the resulting intermediates. The elimination of hydroxyl phosphonates yielded the desired tetrasubstituted olefins in a stereoselective manner. Thus, homofarnesenes of fire ant trail pheromones have been synthesized efficiently using this strategy. ...[more]

PMID: 31458678

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