A Synthesis of the ABC Tricyclic Core of the Clionastatins Serves To Corroborate Their Proposed Structures

[Image: see text] A synthesis of the ABC tricyclic ring system of the clionastatins, an unusual pair of highly chlorinated androstane steroids, has been accomplished. This work provides strong support for the original structural proposal. An unexpected substrate-dependent reversal in alkene chlorina...

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Autores principales: Tartakoff, Samuel S., Vanderwal, Christopher D.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3969099/
https://www.ncbi.nlm.nih.gov/pubmed/24571064
http://dx.doi.org/10.1021/ol500265v
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author Tartakoff, Samuel S.
Vanderwal, Christopher D.
author_facet Tartakoff, Samuel S.
Vanderwal, Christopher D.
author_sort Tartakoff, Samuel S.
collection PubMed
description [Image: see text] A synthesis of the ABC tricyclic ring system of the clionastatins, an unusual pair of highly chlorinated androstane steroids, has been accomplished. This work provides strong support for the original structural proposal. An unexpected substrate-dependent reversal in alkene chlorination diastereoselectivity was critical to success. This approach should be amenable to an eventual enantioselective synthesis of the natural products themselves.
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spelling pubmed-39690992015-02-26 A Synthesis of the ABC Tricyclic Core of the Clionastatins Serves To Corroborate Their Proposed Structures Tartakoff, Samuel S. Vanderwal, Christopher D. Org Lett [Image: see text] A synthesis of the ABC tricyclic ring system of the clionastatins, an unusual pair of highly chlorinated androstane steroids, has been accomplished. This work provides strong support for the original structural proposal. An unexpected substrate-dependent reversal in alkene chlorination diastereoselectivity was critical to success. This approach should be amenable to an eventual enantioselective synthesis of the natural products themselves. American Chemical Society 2014-02-26 2014-03-07 /pmc/articles/PMC3969099/ /pubmed/24571064 http://dx.doi.org/10.1021/ol500265v Text en Copyright © 2014 American Chemical Society
spellingShingle Tartakoff, Samuel S.
Vanderwal, Christopher D.
A Synthesis of the ABC Tricyclic Core of the Clionastatins Serves To Corroborate Their Proposed Structures
title A Synthesis of the ABC Tricyclic Core of the Clionastatins Serves To Corroborate Their Proposed Structures
title_full A Synthesis of the ABC Tricyclic Core of the Clionastatins Serves To Corroborate Their Proposed Structures
title_fullStr A Synthesis of the ABC Tricyclic Core of the Clionastatins Serves To Corroborate Their Proposed Structures
title_full_unstemmed A Synthesis of the ABC Tricyclic Core of the Clionastatins Serves To Corroborate Their Proposed Structures
title_short A Synthesis of the ABC Tricyclic Core of the Clionastatins Serves To Corroborate Their Proposed Structures
title_sort synthesis of the abc tricyclic core of the clionastatins serves to corroborate their proposed structures
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3969099/
https://www.ncbi.nlm.nih.gov/pubmed/24571064
http://dx.doi.org/10.1021/ol500265v
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