The direct oxidative diene cyclization and related reactions in natural product synthesis

The direct oxidative cyclization of 1,5-dienes is a valuable synthetic method for the (dia)stereoselective preparation of substituted tetrahydrofurans. Closely related reactions start from 5,6-dihydroxy or 5-hydroxyalkenes to generate similar products in a mechanistically analogous manner. After a b...

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Detalles Bibliográficos
Autores principales: Adrian, Juliane, Gross, Leona J, Stark, Christian B W
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2016
Materias:
Review
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5082725/
https://www.ncbi.nlm.nih.gov/pubmed/27829917
http://dx.doi.org/10.3762/bjoc.12.200
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author Adrian, Juliane
Gross, Leona J
Stark, Christian B W
author_facet Adrian, Juliane
Gross, Leona J
Stark, Christian B W
author_sort Adrian, Juliane
collection PubMed
description The direct oxidative cyclization of 1,5-dienes is a valuable synthetic method for the (dia)stereoselective preparation of substituted tetrahydrofurans. Closely related reactions start from 5,6-dihydroxy or 5-hydroxyalkenes to generate similar products in a mechanistically analogous manner. After a brief overview on the history of this group of transformations and a survey on mechanistic and stereochemical aspects, this review article provides a summary on applications in natural product synthesis. Moreover, current limitations and future directions in this area of chemistry are discussed.
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spelling pubmed-50827252016-11-09 The direct oxidative diene cyclization and related reactions in natural product synthesis Adrian, Juliane Gross, Leona J Stark, Christian B W Beilstein J Org Chem Review The direct oxidative cyclization of 1,5-dienes is a valuable synthetic method for the (dia)stereoselective preparation of substituted tetrahydrofurans. Closely related reactions start from 5,6-dihydroxy or 5-hydroxyalkenes to generate similar products in a mechanistically analogous manner. After a brief overview on the history of this group of transformations and a survey on mechanistic and stereochemical aspects, this review article provides a summary on applications in natural product synthesis. Moreover, current limitations and future directions in this area of chemistry are discussed. Beilstein-Institut 2016-09-30 /pmc/articles/PMC5082725/ /pubmed/27829917 http://dx.doi.org/10.3762/bjoc.12.200 Text en Copyright © 2016, Adrian et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Review
Adrian, Juliane
Gross, Leona J
Stark, Christian B W
The direct oxidative diene cyclization and related reactions in natural product synthesis
title The direct oxidative diene cyclization and related reactions in natural product synthesis
title_full The direct oxidative diene cyclization and related reactions in natural product synthesis
title_fullStr The direct oxidative diene cyclization and related reactions in natural product synthesis
title_full_unstemmed The direct oxidative diene cyclization and related reactions in natural product synthesis
title_short The direct oxidative diene cyclization and related reactions in natural product synthesis
title_sort direct oxidative diene cyclization and related reactions in natural product synthesis
topic Review
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5082725/
https://www.ncbi.nlm.nih.gov/pubmed/27829917
http://dx.doi.org/10.3762/bjoc.12.200
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