A concise and scalable chemoenzymatic synthesis of prostaglandins
Abstract Prostaglandins have garnered significant attention from synthetic chemists due to their exceptional biological activities. In this report, we present a concise chemoenzymatic synthesis method for several representative prostaglandins, achieved in 5 to 7 steps. Notably, the common intermedia...
| Main Authors: | , , |
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| Format: | Article |
| Language: | English |
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Nature Portfolio
2024-03-01
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| Series: | Nature Communications |
| Online Access: | https://doi.org/10.1038/s41467-024-46960-y |
| _version_ | 1797247165601415168 |
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| author | Yunpeng Yin Jinxin Wang Jian Li |
| author_facet | Yunpeng Yin Jinxin Wang Jian Li |
| author_sort | Yunpeng Yin |
| collection | DOAJ |
| description | Abstract Prostaglandins have garnered significant attention from synthetic chemists due to their exceptional biological activities. In this report, we present a concise chemoenzymatic synthesis method for several representative prostaglandins, achieved in 5 to 7 steps. Notably, the common intermediate bromohydrin, a radical equivalent of Corey lactone, is chemoenzymatically synthesized in only two steps, which allows us to complete the synthesis of prostaglandin F2α in five steps on a 10-gram scale. The chiral cyclopentane core is introduced with high enantioselectivity, while the lipid chains are sequentially incorporated through a cost-effective process involving bromohydrin formation, nickel-catalyzed cross-couplings, and Wittig reactions. This cost-efficient synthesis route for prostaglandins holds the potential to make prostaglandin-related drugs more affordable and facilitate easier access to their analogues. |
| first_indexed | 2024-04-24T19:54:22Z |
| format | Article |
| id | doaj.art-e2cad25c3749465fb3514f8d5acac5e6 |
| institution | Directory Open Access Journal |
| issn | 2041-1723 |
| language | English |
| last_indexed | 2024-04-24T19:54:22Z |
| publishDate | 2024-03-01 |
| publisher | Nature Portfolio |
| record_format | Article |
| series | Nature Communications |
| spelling | doaj.art-e2cad25c3749465fb3514f8d5acac5e62024-03-24T12:26:04ZengNature PortfolioNature Communications2041-17232024-03-011511710.1038/s41467-024-46960-yA concise and scalable chemoenzymatic synthesis of prostaglandinsYunpeng Yin0Jinxin Wang1Jian Li2Frontiers Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs and Zhangjiang Institute for Advanced Study, Shanghai Jiao Tong UniversityDepartment of Phytochemistry, School of Pharmacy, Second Military Medical UniversityFrontiers Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs and Zhangjiang Institute for Advanced Study, Shanghai Jiao Tong UniversityAbstract Prostaglandins have garnered significant attention from synthetic chemists due to their exceptional biological activities. In this report, we present a concise chemoenzymatic synthesis method for several representative prostaglandins, achieved in 5 to 7 steps. Notably, the common intermediate bromohydrin, a radical equivalent of Corey lactone, is chemoenzymatically synthesized in only two steps, which allows us to complete the synthesis of prostaglandin F2α in five steps on a 10-gram scale. The chiral cyclopentane core is introduced with high enantioselectivity, while the lipid chains are sequentially incorporated through a cost-effective process involving bromohydrin formation, nickel-catalyzed cross-couplings, and Wittig reactions. This cost-efficient synthesis route for prostaglandins holds the potential to make prostaglandin-related drugs more affordable and facilitate easier access to their analogues.https://doi.org/10.1038/s41467-024-46960-y |
| spellingShingle | Yunpeng Yin Jinxin Wang Jian Li A concise and scalable chemoenzymatic synthesis of prostaglandins Nature Communications |
| title | A concise and scalable chemoenzymatic synthesis of prostaglandins |
| title_full | A concise and scalable chemoenzymatic synthesis of prostaglandins |
| title_fullStr | A concise and scalable chemoenzymatic synthesis of prostaglandins |
| title_full_unstemmed | A concise and scalable chemoenzymatic synthesis of prostaglandins |
| title_short | A concise and scalable chemoenzymatic synthesis of prostaglandins |
| title_sort | concise and scalable chemoenzymatic synthesis of prostaglandins |
| url | https://doi.org/10.1038/s41467-024-46960-y |
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