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

[Image: see text] 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 hy...

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Autores principales: Yin, Wenhao, Liang, Weihong, Guo, Liping, Lei, Jiaheng, Qiu, Fayang G.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2018
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6641643/
https://www.ncbi.nlm.nih.gov/pubmed/31458678
http://dx.doi.org/10.1021/acsomega.8b00439
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author Yin, Wenhao
Liang, Weihong
Guo, Liping
Lei, Jiaheng
Qiu, Fayang G.
author_facet Yin, Wenhao
Liang, Weihong
Guo, Liping
Lei, Jiaheng
Qiu, Fayang G.
author_sort Yin, Wenhao
collection PubMed
description [Image: see text] 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.
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spelling pubmed-66416432019-08-27 Stereoselective Synthesis of Homofarnesenes: Establishment of an Efficient Method for the Stereoselective Preparation of Acyclic Tetrasubstituted Olefins Yin, Wenhao Liang, Weihong Guo, Liping Lei, Jiaheng Qiu, Fayang G. ACS Omega [Image: see text] 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. American Chemical Society 2018-04-26 /pmc/articles/PMC6641643/ /pubmed/31458678 http://dx.doi.org/10.1021/acsomega.8b00439 Text en Copyright © 2018 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Yin, Wenhao
Liang, Weihong
Guo, Liping
Lei, Jiaheng
Qiu, Fayang G.
Stereoselective Synthesis of Homofarnesenes: Establishment of an Efficient Method for the Stereoselective Preparation of Acyclic Tetrasubstituted Olefins
title Stereoselective Synthesis of Homofarnesenes: Establishment of an Efficient Method for the Stereoselective Preparation of Acyclic Tetrasubstituted Olefins
title_full Stereoselective Synthesis of Homofarnesenes: Establishment of an Efficient Method for the Stereoselective Preparation of Acyclic Tetrasubstituted Olefins
title_fullStr Stereoselective Synthesis of Homofarnesenes: Establishment of an Efficient Method for the Stereoselective Preparation of Acyclic Tetrasubstituted Olefins
title_full_unstemmed Stereoselective Synthesis of Homofarnesenes: Establishment of an Efficient Method for the Stereoselective Preparation of Acyclic Tetrasubstituted Olefins
title_short Stereoselective Synthesis of Homofarnesenes: Establishment of an Efficient Method for the Stereoselective Preparation of Acyclic Tetrasubstituted Olefins
title_sort stereoselective synthesis of homofarnesenes: establishment of an efficient method for the stereoselective preparation of acyclic tetrasubstituted olefins
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6641643/
https://www.ncbi.nlm.nih.gov/pubmed/31458678
http://dx.doi.org/10.1021/acsomega.8b00439
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