Synthesis of the ABCDEF and FGHI ring system of yessotoxin and adriatoxin

Yessotoxin and adriatoxin are members of the polycyclic ether family of marine natural products. Outlined in this article is our synthetic approach to two subunits of these targets. Central to our strategy is a coupling sequence that employs an olefinic-ester cyclization reaction. As outlined, this...

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Detalles Bibliográficos
Autores principales: Zhang, Yuan, Rainier, Jon D.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: 2016
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4898783/
https://www.ncbi.nlm.nih.gov/pubmed/26956788
http://dx.doi.org/10.1038/ja.2016.18
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author Zhang, Yuan
Rainier, Jon D.
author_facet Zhang, Yuan
Rainier, Jon D.
author_sort Zhang, Yuan
collection PubMed
description Yessotoxin and adriatoxin are members of the polycyclic ether family of marine natural products. Outlined in this article is our synthetic approach to two subunits of these targets. Central to our strategy is a coupling sequence that employs an olefinic-ester cyclization reaction. As outlined, this sequence was used in two coupling sequences. First it was used to merge the A,B- and E,F-bicyclic precursors and in the process generate the C, D-rings. Second it was used to couple the F- and I-rings while building the eight-membered G-ring and subsequently the H-ring pyran.
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spelling pubmed-48987832016-09-09 Synthesis of the ABCDEF and FGHI ring system of yessotoxin and adriatoxin Zhang, Yuan Rainier, Jon D. J Antibiot (Tokyo) Article Yessotoxin and adriatoxin are members of the polycyclic ether family of marine natural products. Outlined in this article is our synthetic approach to two subunits of these targets. Central to our strategy is a coupling sequence that employs an olefinic-ester cyclization reaction. As outlined, this sequence was used in two coupling sequences. First it was used to merge the A,B- and E,F-bicyclic precursors and in the process generate the C, D-rings. Second it was used to couple the F- and I-rings while building the eight-membered G-ring and subsequently the H-ring pyran. 2016-03-09 2016-04 /pmc/articles/PMC4898783/ /pubmed/26956788 http://dx.doi.org/10.1038/ja.2016.18 Text en Users may view, print, copy, and download text and data-mine the content in such documents, for the purposes of academic research, subject always to the full Conditions of use: http://www.nature.com/authors/editorial_policies/license.html#terms
spellingShingle Article
Zhang, Yuan
Rainier, Jon D.
Synthesis of the ABCDEF and FGHI ring system of yessotoxin and adriatoxin
title Synthesis of the ABCDEF and FGHI ring system of yessotoxin and adriatoxin
title_full Synthesis of the ABCDEF and FGHI ring system of yessotoxin and adriatoxin
title_fullStr Synthesis of the ABCDEF and FGHI ring system of yessotoxin and adriatoxin
title_full_unstemmed Synthesis of the ABCDEF and FGHI ring system of yessotoxin and adriatoxin
title_short Synthesis of the ABCDEF and FGHI ring system of yessotoxin and adriatoxin
title_sort synthesis of the abcdef and fghi ring system of yessotoxin and adriatoxin
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4898783/
https://www.ncbi.nlm.nih.gov/pubmed/26956788
http://dx.doi.org/10.1038/ja.2016.18
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