Total synthesis of the reported structure of 13a-hydroxytylophorine

The first total synthesis of the reported structure of 13a-hydroxytylophorine was accomplished. The key step was an unprecedented NaBH(4)-promoted one-pot reductive cyclization cascade that efficiently yielded a hydroxyl azonane intermediate. The indolizidine framework was obtained by means of oxida...

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Autores principales: Zhang, Hui, Li, Gang, Su, Bo, Deng, Meng, Liu, Yu-Xiu, Gu, Yu-Cheng, Wang, Qing-Min
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2017
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5716997/
https://www.ncbi.nlm.nih.gov/pubmed/29208905
http://dx.doi.org/10.1038/s41598-017-17015-8
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author Zhang, Hui
Li, Gang
Su, Bo
Deng, Meng
Liu, Yu-Xiu
Gu, Yu-Cheng
Wang, Qing-Min
author_facet Zhang, Hui
Li, Gang
Su, Bo
Deng, Meng
Liu, Yu-Xiu
Gu, Yu-Cheng
Wang, Qing-Min
author_sort Zhang, Hui
collection PubMed
description The first total synthesis of the reported structure of 13a-hydroxytylophorine was accomplished. The key step was an unprecedented NaBH(4)-promoted one-pot reductive cyclization cascade that efficiently yielded a hydroxyl azonane intermediate. The indolizidine framework was obtained by means of oxidation and a subsequent unexpected protecting-group migration. This total synthesis revealed that the reported structure of the naturally isolated compound is incorrect.
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spelling pubmed-57169972017-12-08 Total synthesis of the reported structure of 13a-hydroxytylophorine Zhang, Hui Li, Gang Su, Bo Deng, Meng Liu, Yu-Xiu Gu, Yu-Cheng Wang, Qing-Min Sci Rep Article The first total synthesis of the reported structure of 13a-hydroxytylophorine was accomplished. The key step was an unprecedented NaBH(4)-promoted one-pot reductive cyclization cascade that efficiently yielded a hydroxyl azonane intermediate. The indolizidine framework was obtained by means of oxidation and a subsequent unexpected protecting-group migration. This total synthesis revealed that the reported structure of the naturally isolated compound is incorrect. Nature Publishing Group UK 2017-12-05 /pmc/articles/PMC5716997/ /pubmed/29208905 http://dx.doi.org/10.1038/s41598-017-17015-8 Text en © The Author(s) 2017 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
Zhang, Hui
Li, Gang
Su, Bo
Deng, Meng
Liu, Yu-Xiu
Gu, Yu-Cheng
Wang, Qing-Min
Total synthesis of the reported structure of 13a-hydroxytylophorine
title Total synthesis of the reported structure of 13a-hydroxytylophorine
title_full Total synthesis of the reported structure of 13a-hydroxytylophorine
title_fullStr Total synthesis of the reported structure of 13a-hydroxytylophorine
title_full_unstemmed Total synthesis of the reported structure of 13a-hydroxytylophorine
title_short Total synthesis of the reported structure of 13a-hydroxytylophorine
title_sort total synthesis of the reported structure of 13a-hydroxytylophorine
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5716997/
https://www.ncbi.nlm.nih.gov/pubmed/29208905
http://dx.doi.org/10.1038/s41598-017-17015-8
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