A unified strategy toward total syntheses of lindenane sesquiterpenoid [4 + 2] dimers

The dimeric lindenane sesquiterpenoids are mainly isolated from the plants of Chloranthaceae family. Structurally, they have a crowded molecular scaffold decorated with more than 11 stereogenic centers. Here we report divergent syntheses of eight dimeric lindenane sesquiterpenoids, shizukaols A, C,...

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Autores principales: Du, Biao, Huang, Zhengsong, Wang, Xiao, Chen, Ting, Shen, Guo, Fu, Shaomin, Liu, Bo
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2019
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6478710/
https://www.ncbi.nlm.nih.gov/pubmed/31015442
http://dx.doi.org/10.1038/s41467-019-09858-8
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author Du, Biao
Huang, Zhengsong
Wang, Xiao
Chen, Ting
Shen, Guo
Fu, Shaomin
Liu, Bo
author_facet Du, Biao
Huang, Zhengsong
Wang, Xiao
Chen, Ting
Shen, Guo
Fu, Shaomin
Liu, Bo
author_sort Du, Biao
collection PubMed
description The dimeric lindenane sesquiterpenoids are mainly isolated from the plants of Chloranthaceae family. Structurally, they have a crowded molecular scaffold decorated with more than 11 stereogenic centers. Here we report divergent syntheses of eight dimeric lindenane sesquiterpenoids, shizukaols A, C, D, I, chlorajaponilide C, multistalide B, sarcandrolide J and sarglabolide I. In particular, we present a unified dimerization strategy utilizing a base-mediated thermal [4 + 2] cycloaddition between a common furyl diene, generated in situ, and various types of dienophiles. Accordingly, all the three types of lindenane [4 + 2] dimers with versatile biological activities are accessible, which would stimulate future probing of their pharmaceutical potential.
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spelling pubmed-64787102019-04-25 A unified strategy toward total syntheses of lindenane sesquiterpenoid [4 + 2] dimers Du, Biao Huang, Zhengsong Wang, Xiao Chen, Ting Shen, Guo Fu, Shaomin Liu, Bo Nat Commun Article The dimeric lindenane sesquiterpenoids are mainly isolated from the plants of Chloranthaceae family. Structurally, they have a crowded molecular scaffold decorated with more than 11 stereogenic centers. Here we report divergent syntheses of eight dimeric lindenane sesquiterpenoids, shizukaols A, C, D, I, chlorajaponilide C, multistalide B, sarcandrolide J and sarglabolide I. In particular, we present a unified dimerization strategy utilizing a base-mediated thermal [4 + 2] cycloaddition between a common furyl diene, generated in situ, and various types of dienophiles. Accordingly, all the three types of lindenane [4 + 2] dimers with versatile biological activities are accessible, which would stimulate future probing of their pharmaceutical potential. Nature Publishing Group UK 2019-04-23 /pmc/articles/PMC6478710/ /pubmed/31015442 http://dx.doi.org/10.1038/s41467-019-09858-8 Text en © The Author(s) 2019 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
Du, Biao
Huang, Zhengsong
Wang, Xiao
Chen, Ting
Shen, Guo
Fu, Shaomin
Liu, Bo
A unified strategy toward total syntheses of lindenane sesquiterpenoid [4 + 2] dimers
title A unified strategy toward total syntheses of lindenane sesquiterpenoid [4 + 2] dimers
title_full A unified strategy toward total syntheses of lindenane sesquiterpenoid [4 + 2] dimers
title_fullStr A unified strategy toward total syntheses of lindenane sesquiterpenoid [4 + 2] dimers
title_full_unstemmed A unified strategy toward total syntheses of lindenane sesquiterpenoid [4 + 2] dimers
title_short A unified strategy toward total syntheses of lindenane sesquiterpenoid [4 + 2] dimers
title_sort unified strategy toward total syntheses of lindenane sesquiterpenoid [4 + 2] dimers
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6478710/
https://www.ncbi.nlm.nih.gov/pubmed/31015442
http://dx.doi.org/10.1038/s41467-019-09858-8
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