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Asymmetric synthesis of chromanone lactones via vinylogous conjugate addition of butenolide to 2-ester chromones

Chiral chromanone lactones are a class of natural products with important biological activity. We report a direct diastereo- and enantioselective vinylogous conjugate addition of butenolide to 2-ester substituted chromones. The transformation proceeded well in the presence of as low as 1 mol% of a c...

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Detalles Bibliográficos
Autores principales: Li, Yi, Xin, Shuang, Weng, Rui, Liu, Xiaohua, Feng, Xiaoming
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9350614/
https://www.ncbi.nlm.nih.gov/pubmed/35975160
http://dx.doi.org/10.1039/d2sc02541h
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author Li, Yi
Xin, Shuang
Weng, Rui
Liu, Xiaohua
Feng, Xiaoming
author_facet Li, Yi
Xin, Shuang
Weng, Rui
Liu, Xiaohua
Feng, Xiaoming
author_sort Li, Yi
collection PubMed
description Chiral chromanone lactones are a class of natural products with important biological activity. We report a direct diastereo- and enantioselective vinylogous conjugate addition of butenolide to 2-ester substituted chromones. The transformation proceeded well in the presence of as low as 1 mol% of a chiral N,N′-dioxide/Sc(III) complex, 3 Å MS and a catalytic amount of hexafluoroisopropanol (HFIP). The scope of Michael acceptors includes a variety of substituted chromones at different positions, and the desired chromanone lactones upon reduction are afforded in good yield and diastereoselectivity, and excellent enantioselectivity (up to 99% ee). The strategy could be used in the concise synthesis of blennolide C and gonytolide A, C and G.
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spelling pubmed-93506142022-08-15 Asymmetric synthesis of chromanone lactones via vinylogous conjugate addition of butenolide to 2-ester chromones Li, Yi Xin, Shuang Weng, Rui Liu, Xiaohua Feng, Xiaoming Chem Sci Chemistry Chiral chromanone lactones are a class of natural products with important biological activity. We report a direct diastereo- and enantioselective vinylogous conjugate addition of butenolide to 2-ester substituted chromones. The transformation proceeded well in the presence of as low as 1 mol% of a chiral N,N′-dioxide/Sc(III) complex, 3 Å MS and a catalytic amount of hexafluoroisopropanol (HFIP). The scope of Michael acceptors includes a variety of substituted chromones at different positions, and the desired chromanone lactones upon reduction are afforded in good yield and diastereoselectivity, and excellent enantioselectivity (up to 99% ee). The strategy could be used in the concise synthesis of blennolide C and gonytolide A, C and G. The Royal Society of Chemistry 2022-07-05 /pmc/articles/PMC9350614/ /pubmed/35975160 http://dx.doi.org/10.1039/d2sc02541h Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Li, Yi
Xin, Shuang
Weng, Rui
Liu, Xiaohua
Feng, Xiaoming
Asymmetric synthesis of chromanone lactones via vinylogous conjugate addition of butenolide to 2-ester chromones
title Asymmetric synthesis of chromanone lactones via vinylogous conjugate addition of butenolide to 2-ester chromones
title_full Asymmetric synthesis of chromanone lactones via vinylogous conjugate addition of butenolide to 2-ester chromones
title_fullStr Asymmetric synthesis of chromanone lactones via vinylogous conjugate addition of butenolide to 2-ester chromones
title_full_unstemmed Asymmetric synthesis of chromanone lactones via vinylogous conjugate addition of butenolide to 2-ester chromones
title_short Asymmetric synthesis of chromanone lactones via vinylogous conjugate addition of butenolide to 2-ester chromones
title_sort asymmetric synthesis of chromanone lactones via vinylogous conjugate addition of butenolide to 2-ester chromones
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9350614/
https://www.ncbi.nlm.nih.gov/pubmed/35975160
http://dx.doi.org/10.1039/d2sc02541h
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