Study on the total synthesis of velbanamine: Chemoselective dioxygenation of alkenes with PIFA via a stop-and-flow strategy

A “stop-and-flow” strategy was developed for the chemoselective dioxygenation of alkenes with a PIFA-initiated cyclization. This method is conceived for the desymmetrization of seco-diene, and a series of substituted 5-hydroxymethyl-γ-lactones were constructed after hydrolysis. This strategy also di...

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Detalles Bibliográficos
Autores principales: Liu, Huili, Zheng, Kuan, Lu, Xiang, Wang, Xiaoxia, Hong, Ran
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2013
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3678578/
https://www.ncbi.nlm.nih.gov/pubmed/23766815
http://dx.doi.org/10.3762/bjoc.9.113
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author Liu, Huili
Zheng, Kuan
Lu, Xiang
Wang, Xiaoxia
Hong, Ran
author_facet Liu, Huili
Zheng, Kuan
Lu, Xiang
Wang, Xiaoxia
Hong, Ran
author_sort Liu, Huili
collection PubMed
description A “stop-and-flow” strategy was developed for the chemoselective dioxygenation of alkenes with a PIFA-initiated cyclization. This method is conceived for the desymmetrization of seco-diene, and a series of substituted 5-hydroxymethyl-γ-lactones were constructed after hydrolysis. This strategy also differentiates terminally substituted alkenes and constitutes a potentially novel synthetic approach for the efficient synthesis toward velbanamine.
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spelling pubmed-36785782013-06-13 Study on the total synthesis of velbanamine: Chemoselective dioxygenation of alkenes with PIFA via a stop-and-flow strategy Liu, Huili Zheng, Kuan Lu, Xiang Wang, Xiaoxia Hong, Ran Beilstein J Org Chem Full Research Paper A “stop-and-flow” strategy was developed for the chemoselective dioxygenation of alkenes with a PIFA-initiated cyclization. This method is conceived for the desymmetrization of seco-diene, and a series of substituted 5-hydroxymethyl-γ-lactones were constructed after hydrolysis. This strategy also differentiates terminally substituted alkenes and constitutes a potentially novel synthetic approach for the efficient synthesis toward velbanamine. Beilstein-Institut 2013-05-23 /pmc/articles/PMC3678578/ /pubmed/23766815 http://dx.doi.org/10.3762/bjoc.9.113 Text en Copyright © 2013, Liu et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Liu, Huili
Zheng, Kuan
Lu, Xiang
Wang, Xiaoxia
Hong, Ran
Study on the total synthesis of velbanamine: Chemoselective dioxygenation of alkenes with PIFA via a stop-and-flow strategy
title Study on the total synthesis of velbanamine: Chemoselective dioxygenation of alkenes with PIFA via a stop-and-flow strategy
title_full Study on the total synthesis of velbanamine: Chemoselective dioxygenation of alkenes with PIFA via a stop-and-flow strategy
title_fullStr Study on the total synthesis of velbanamine: Chemoselective dioxygenation of alkenes with PIFA via a stop-and-flow strategy
title_full_unstemmed Study on the total synthesis of velbanamine: Chemoselective dioxygenation of alkenes with PIFA via a stop-and-flow strategy
title_short Study on the total synthesis of velbanamine: Chemoselective dioxygenation of alkenes with PIFA via a stop-and-flow strategy
title_sort study on the total synthesis of velbanamine: chemoselective dioxygenation of alkenes with pifa via a stop-and-flow strategy
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3678578/
https://www.ncbi.nlm.nih.gov/pubmed/23766815
http://dx.doi.org/10.3762/bjoc.9.113
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