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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...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2022
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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. |
format | Online Article Text |
id | pubmed-9350614 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
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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