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Pot and time economies in the total synthesis of Corey lactone
The Corey lactone is a highly versatile intermediate for the synthesis of a variety of prostaglandin hormones that natively control a multitude of important physiological processes. Starting from commercially available compounds, we herein disclose a time-economical, one-pot enantioselective prepara...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2019
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8148033/ https://www.ncbi.nlm.nih.gov/pubmed/34123244 http://dx.doi.org/10.1039/c9sc05824a |
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author | Umekubo, Nariyoshi Suga, Yurina Hayashi, Yujiro |
author_facet | Umekubo, Nariyoshi Suga, Yurina Hayashi, Yujiro |
author_sort | Umekubo, Nariyoshi |
collection | PubMed |
description | The Corey lactone is a highly versatile intermediate for the synthesis of a variety of prostaglandin hormones that natively control a multitude of important physiological processes. Starting from commercially available compounds, we herein disclose a time-economical, one-pot enantioselective preparation of the Corey lactone by virtue of a new diphenylprolinol silyl ether-mediated domino Michael/Michael reaction to afford the substituted cyclopentanone core in a formal (3 + 2) cycloadditive fashion. More broadly, this work advances the on-demand, gram-scale synthesis of high-value targets involving chemically orthogonal transformations, whereby distinct reactions of acids, bases, organometalics, reductants and oxidants can be carried out in a single reaction vessel in a sequential fashion. |
format | Online Article Text |
id | pubmed-8148033 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-81480332021-06-11 Pot and time economies in the total synthesis of Corey lactone Umekubo, Nariyoshi Suga, Yurina Hayashi, Yujiro Chem Sci Chemistry The Corey lactone is a highly versatile intermediate for the synthesis of a variety of prostaglandin hormones that natively control a multitude of important physiological processes. Starting from commercially available compounds, we herein disclose a time-economical, one-pot enantioselective preparation of the Corey lactone by virtue of a new diphenylprolinol silyl ether-mediated domino Michael/Michael reaction to afford the substituted cyclopentanone core in a formal (3 + 2) cycloadditive fashion. More broadly, this work advances the on-demand, gram-scale synthesis of high-value targets involving chemically orthogonal transformations, whereby distinct reactions of acids, bases, organometalics, reductants and oxidants can be carried out in a single reaction vessel in a sequential fashion. The Royal Society of Chemistry 2019-12-23 /pmc/articles/PMC8148033/ /pubmed/34123244 http://dx.doi.org/10.1039/c9sc05824a Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/ |
spellingShingle | Chemistry Umekubo, Nariyoshi Suga, Yurina Hayashi, Yujiro Pot and time economies in the total synthesis of Corey lactone |
title | Pot and time economies in the total synthesis of Corey lactone |
title_full | Pot and time economies in the total synthesis of Corey lactone |
title_fullStr | Pot and time economies in the total synthesis of Corey lactone |
title_full_unstemmed | Pot and time economies in the total synthesis of Corey lactone |
title_short | Pot and time economies in the total synthesis of Corey lactone |
title_sort | pot and time economies in the total synthesis of corey lactone |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8148033/ https://www.ncbi.nlm.nih.gov/pubmed/34123244 http://dx.doi.org/10.1039/c9sc05824a |
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