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Catalytic Asymmetric Synthesis of Butenolides and Butyrolactones
[Image: see text] γ-Butenolides, γ-butyrolactones, and derivatives, especially in enantiomerically pure form, constitute the structural core of numerous natural products which display an impressive range of biological activities which are important for the development of novel physiological and ther...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American
Chemical Society
2017
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5553117/ https://www.ncbi.nlm.nih.gov/pubmed/28640622 http://dx.doi.org/10.1021/acs.chemrev.7b00151 |
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author | Mao, Bin Fañanás-Mastral, Martín Feringa, Ben L. |
author_facet | Mao, Bin Fañanás-Mastral, Martín Feringa, Ben L. |
author_sort | Mao, Bin |
collection | PubMed |
description | [Image: see text] γ-Butenolides, γ-butyrolactones, and derivatives, especially in enantiomerically pure form, constitute the structural core of numerous natural products which display an impressive range of biological activities which are important for the development of novel physiological and therapeutic agents. Furthermore, optically active γ-butenolides and γ-butyrolactones serve also as a prominent class of chiral building blocks for the synthesis of diverse biological active compounds and complex molecules. Taking into account the varying biological activity profiles and wide-ranging structural diversity of the optically active γ-butenolide or γ-butyrolactone structure, the development of asymmetric synthetic strategies for assembling such challenging scaffolds has attracted major attention from synthetic chemists in the past decade. This review offers an overview of the different enantioselective synthesis of γ-butenolides and γ-butyrolactones which employ catalytic amounts of metal complexes or organocatalysts, with emphasis focused on the mechanistic issues that account for the observed stereocontrol of the representative reactions, as well as practical applications and synthetic potentials. |
format | Online Article Text |
id | pubmed-5553117 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | American
Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-55531172017-08-14 Catalytic Asymmetric Synthesis of Butenolides and Butyrolactones Mao, Bin Fañanás-Mastral, Martín Feringa, Ben L. Chem Rev [Image: see text] γ-Butenolides, γ-butyrolactones, and derivatives, especially in enantiomerically pure form, constitute the structural core of numerous natural products which display an impressive range of biological activities which are important for the development of novel physiological and therapeutic agents. Furthermore, optically active γ-butenolides and γ-butyrolactones serve also as a prominent class of chiral building blocks for the synthesis of diverse biological active compounds and complex molecules. Taking into account the varying biological activity profiles and wide-ranging structural diversity of the optically active γ-butenolide or γ-butyrolactone structure, the development of asymmetric synthetic strategies for assembling such challenging scaffolds has attracted major attention from synthetic chemists in the past decade. This review offers an overview of the different enantioselective synthesis of γ-butenolides and γ-butyrolactones which employ catalytic amounts of metal complexes or organocatalysts, with emphasis focused on the mechanistic issues that account for the observed stereocontrol of the representative reactions, as well as practical applications and synthetic potentials. American Chemical Society 2017-06-22 2017-08-09 /pmc/articles/PMC5553117/ /pubmed/28640622 http://dx.doi.org/10.1021/acs.chemrev.7b00151 Text en Copyright © 2017 American Chemical Society This is an open access article published under a Creative Commons Non-Commercial No Derivative Works (CC-BY-NC-ND) Attribution License (http://pubs.acs.org/page/policy/authorchoice_ccbyncnd_termsofuse.html) , which permits copying and redistribution of the article, and creation of adaptations, all for non-commercial purposes. |
spellingShingle | Mao, Bin Fañanás-Mastral, Martín Feringa, Ben L. Catalytic Asymmetric Synthesis of Butenolides and Butyrolactones |
title | Catalytic Asymmetric Synthesis of Butenolides and
Butyrolactones |
title_full | Catalytic Asymmetric Synthesis of Butenolides and
Butyrolactones |
title_fullStr | Catalytic Asymmetric Synthesis of Butenolides and
Butyrolactones |
title_full_unstemmed | Catalytic Asymmetric Synthesis of Butenolides and
Butyrolactones |
title_short | Catalytic Asymmetric Synthesis of Butenolides and
Butyrolactones |
title_sort | catalytic asymmetric synthesis of butenolides and
butyrolactones |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5553117/ https://www.ncbi.nlm.nih.gov/pubmed/28640622 http://dx.doi.org/10.1021/acs.chemrev.7b00151 |
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