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Concise synthesis of the A/BCD-ring fragment of gambieric acid A
Gambieric acid A (GAA) and its congeners belong to the family of marine polycyclic ether natural products. Their highly complex molecular architecture and unique biological activities have been of intense interest within the synthetic community. We have previously reported the first total synthesis,...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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Frontiers Media S.A.
2015
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4292782/ https://www.ncbi.nlm.nih.gov/pubmed/25629027 http://dx.doi.org/10.3389/fchem.2014.00116 |
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author | Fuwa, Haruhiko Fukazawa, Ryo Sasaki, Makoto |
author_facet | Fuwa, Haruhiko Fukazawa, Ryo Sasaki, Makoto |
author_sort | Fuwa, Haruhiko |
collection | PubMed |
description | Gambieric acid A (GAA) and its congeners belong to the family of marine polycyclic ether natural products. Their highly complex molecular architecture and unique biological activities have been of intense interest within the synthetic community. We have previously reported the first total synthesis, stereochemical reassignment, and preliminary structure–activity relationships of GAA. Here we disclose a concise synthesis of the A/BCD-ring fragment of GAA. The synthesis started from our previously reported synthetic intermediate that represents the A/B-ring. The C-ring was synthesized via an oxiranyl anion coupling and a 6-endo cyclization, and the D-ring was forged by means of an oxidative lactonization and subsequent palladium-catalyzed functionalization of the lactone ring. In this manner, the number of linear synthetic steps required for the construction of the C- and D-rings was reduced from 22 to 11. |
format | Online Article Text |
id | pubmed-4292782 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2015 |
publisher | Frontiers Media S.A. |
record_format | MEDLINE/PubMed |
spelling | pubmed-42927822015-01-27 Concise synthesis of the A/BCD-ring fragment of gambieric acid A Fuwa, Haruhiko Fukazawa, Ryo Sasaki, Makoto Front Chem Chemistry Gambieric acid A (GAA) and its congeners belong to the family of marine polycyclic ether natural products. Their highly complex molecular architecture and unique biological activities have been of intense interest within the synthetic community. We have previously reported the first total synthesis, stereochemical reassignment, and preliminary structure–activity relationships of GAA. Here we disclose a concise synthesis of the A/BCD-ring fragment of GAA. The synthesis started from our previously reported synthetic intermediate that represents the A/B-ring. The C-ring was synthesized via an oxiranyl anion coupling and a 6-endo cyclization, and the D-ring was forged by means of an oxidative lactonization and subsequent palladium-catalyzed functionalization of the lactone ring. In this manner, the number of linear synthetic steps required for the construction of the C- and D-rings was reduced from 22 to 11. Frontiers Media S.A. 2015-01-13 /pmc/articles/PMC4292782/ /pubmed/25629027 http://dx.doi.org/10.3389/fchem.2014.00116 Text en Copyright © 2015 Fuwa, Fukazawa and Sasaki. http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) or licensor are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms. |
spellingShingle | Chemistry Fuwa, Haruhiko Fukazawa, Ryo Sasaki, Makoto Concise synthesis of the A/BCD-ring fragment of gambieric acid A |
title | Concise synthesis of the A/BCD-ring fragment of gambieric acid A |
title_full | Concise synthesis of the A/BCD-ring fragment of gambieric acid A |
title_fullStr | Concise synthesis of the A/BCD-ring fragment of gambieric acid A |
title_full_unstemmed | Concise synthesis of the A/BCD-ring fragment of gambieric acid A |
title_short | Concise synthesis of the A/BCD-ring fragment of gambieric acid A |
title_sort | concise synthesis of the a/bcd-ring fragment of gambieric acid a |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4292782/ https://www.ncbi.nlm.nih.gov/pubmed/25629027 http://dx.doi.org/10.3389/fchem.2014.00116 |
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