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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...

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Autores principales: Mao, Bin, Fañanás-Mastral, Martín, Feringa, Ben L.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2017
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.
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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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