Ti-Catalyzed Cross-Cyclomagnesiation of 1,2-Dienes in the Total Z,Z,Z-Stereoselective Synthesis of Natural Acetogenin–Chatenaytrienin-1

[Image: see text] The first total synthesis of natural acetogenin, chatenaytrienin-1, was performed in 10 steps and in 41% overall yield using cross-cyclomagnesiation of (6Z)-heptadeca-1,2,6-triene and trideca-11,12-dien-1-ol tetrahydropyran acetal with EtMgBr in the presence of Mg metal and the Cp(...

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Autores principales: D’yakonov, Vladimir A., Tuktarova, Regina A., Dzhemilev, Usein M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2019
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6714518/
https://www.ncbi.nlm.nih.gov/pubmed/31497727
http://dx.doi.org/10.1021/acsomega.9b01951
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author D’yakonov, Vladimir A.
Tuktarova, Regina A.
Dzhemilev, Usein M.
author_facet D’yakonov, Vladimir A.
Tuktarova, Regina A.
Dzhemilev, Usein M.
author_sort D’yakonov, Vladimir A.
collection PubMed
description [Image: see text] The first total synthesis of natural acetogenin, chatenaytrienin-1, was performed in 10 steps and in 41% overall yield using cross-cyclomagnesiation of (6Z)-heptadeca-1,2,6-triene and trideca-11,12-dien-1-ol tetrahydropyran acetal with EtMgBr in the presence of Mg metal and the Cp(2)TiCl(2) catalyst (10 mol %) as the key step of the synthesis.
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spelling pubmed-67145182019-09-06 Ti-Catalyzed Cross-Cyclomagnesiation of 1,2-Dienes in the Total Z,Z,Z-Stereoselective Synthesis of Natural Acetogenin–Chatenaytrienin-1 D’yakonov, Vladimir A. Tuktarova, Regina A. Dzhemilev, Usein M. ACS Omega [Image: see text] The first total synthesis of natural acetogenin, chatenaytrienin-1, was performed in 10 steps and in 41% overall yield using cross-cyclomagnesiation of (6Z)-heptadeca-1,2,6-triene and trideca-11,12-dien-1-ol tetrahydropyran acetal with EtMgBr in the presence of Mg metal and the Cp(2)TiCl(2) catalyst (10 mol %) as the key step of the synthesis. American Chemical Society 2019-08-16 /pmc/articles/PMC6714518/ /pubmed/31497727 http://dx.doi.org/10.1021/acsomega.9b01951 Text en Copyright © 2019 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 D’yakonov, Vladimir A.
Tuktarova, Regina A.
Dzhemilev, Usein M.
Ti-Catalyzed Cross-Cyclomagnesiation of 1,2-Dienes in the Total Z,Z,Z-Stereoselective Synthesis of Natural Acetogenin–Chatenaytrienin-1
title Ti-Catalyzed Cross-Cyclomagnesiation of 1,2-Dienes in the Total Z,Z,Z-Stereoselective Synthesis of Natural Acetogenin–Chatenaytrienin-1
title_full Ti-Catalyzed Cross-Cyclomagnesiation of 1,2-Dienes in the Total Z,Z,Z-Stereoselective Synthesis of Natural Acetogenin–Chatenaytrienin-1
title_fullStr Ti-Catalyzed Cross-Cyclomagnesiation of 1,2-Dienes in the Total Z,Z,Z-Stereoselective Synthesis of Natural Acetogenin–Chatenaytrienin-1
title_full_unstemmed Ti-Catalyzed Cross-Cyclomagnesiation of 1,2-Dienes in the Total Z,Z,Z-Stereoselective Synthesis of Natural Acetogenin–Chatenaytrienin-1
title_short Ti-Catalyzed Cross-Cyclomagnesiation of 1,2-Dienes in the Total Z,Z,Z-Stereoselective Synthesis of Natural Acetogenin–Chatenaytrienin-1
title_sort ti-catalyzed cross-cyclomagnesiation of 1,2-dienes in the total z,z,z-stereoselective synthesis of natural acetogenin–chatenaytrienin-1
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6714518/
https://www.ncbi.nlm.nih.gov/pubmed/31497727
http://dx.doi.org/10.1021/acsomega.9b01951
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