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Programmable meroterpene synthesis
The bicyclo[3.3.1]nonane architecture is a privileged structural motif found in over 1000 natural products with relevance to neurodegenerative disease, bacterial and parasitic infection, and cancer among others. Despite disparate biosynthetic machinery, alkaloid, terpene, and polyketide-producing or...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Nature Publishing Group UK
2020
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6981159/ https://www.ncbi.nlm.nih.gov/pubmed/31980637 http://dx.doi.org/10.1038/s41467-020-14354-5 |
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author | Shen, Xingyu Ting, Chi P. Xu, Gong Maimone, Thomas J. |
author_facet | Shen, Xingyu Ting, Chi P. Xu, Gong Maimone, Thomas J. |
author_sort | Shen, Xingyu |
collection | PubMed |
description | The bicyclo[3.3.1]nonane architecture is a privileged structural motif found in over 1000 natural products with relevance to neurodegenerative disease, bacterial and parasitic infection, and cancer among others. Despite disparate biosynthetic machinery, alkaloid, terpene, and polyketide-producing organisms have all evolved pathways to incorporate this carbocyclic ring system. Natural products of mixed polyketide/terpenoid origins (meroterpenes) are a particularly rich and important source of biologically active bicyclo[3.3.1]nonane-containing molecules. Herein we detail a fully synthetic strategy toward this broad family of targets based on an abiotic annulation/rearrangement strategy resulting in a 10-step total synthesis of garsubellin A, an enhancer of choline acetyltransferase and member of the large family of polycyclic polyprenylated acylphloroglucinols. This work solidifies a strategy for making multiple, diverse meroterpene chemotypes in a programmable assembly process involving a minimal number of chemical transformations. |
format | Online Article Text |
id | pubmed-6981159 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | Nature Publishing Group UK |
record_format | MEDLINE/PubMed |
spelling | pubmed-69811592020-01-27 Programmable meroterpene synthesis Shen, Xingyu Ting, Chi P. Xu, Gong Maimone, Thomas J. Nat Commun Article The bicyclo[3.3.1]nonane architecture is a privileged structural motif found in over 1000 natural products with relevance to neurodegenerative disease, bacterial and parasitic infection, and cancer among others. Despite disparate biosynthetic machinery, alkaloid, terpene, and polyketide-producing organisms have all evolved pathways to incorporate this carbocyclic ring system. Natural products of mixed polyketide/terpenoid origins (meroterpenes) are a particularly rich and important source of biologically active bicyclo[3.3.1]nonane-containing molecules. Herein we detail a fully synthetic strategy toward this broad family of targets based on an abiotic annulation/rearrangement strategy resulting in a 10-step total synthesis of garsubellin A, an enhancer of choline acetyltransferase and member of the large family of polycyclic polyprenylated acylphloroglucinols. This work solidifies a strategy for making multiple, diverse meroterpene chemotypes in a programmable assembly process involving a minimal number of chemical transformations. Nature Publishing Group UK 2020-01-24 /pmc/articles/PMC6981159/ /pubmed/31980637 http://dx.doi.org/10.1038/s41467-020-14354-5 Text en © The Author(s) 2020 Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/. |
spellingShingle | Article Shen, Xingyu Ting, Chi P. Xu, Gong Maimone, Thomas J. Programmable meroterpene synthesis |
title | Programmable meroterpene synthesis |
title_full | Programmable meroterpene synthesis |
title_fullStr | Programmable meroterpene synthesis |
title_full_unstemmed | Programmable meroterpene synthesis |
title_short | Programmable meroterpene synthesis |
title_sort | programmable meroterpene synthesis |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6981159/ https://www.ncbi.nlm.nih.gov/pubmed/31980637 http://dx.doi.org/10.1038/s41467-020-14354-5 |
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