An asymmetric Suzuki-Miyaura approach to prostaglandins: Synthesis of Tafluprost
We report the catalytic asymmetric synthesis of Tafluprost (1), a prostaglandin analogue. This synthesis demonstrates a new approach to prostaglandins involving symmetrization and desymmetrization of a racemic precursor to control the absolute and relative stereochemistry of the cyclopentyl core. Ke...
| 主要な著者: | , , |
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| フォーマット: | Journal article |
| 言語: | English |
| 出版事項: |
American Chemical Society
2020
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| _version_ | 1826267637904048128 |
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| author | Kučera, R Goetzke, FW Fletcher, SP |
| author_facet | Kučera, R Goetzke, FW Fletcher, SP |
| author_sort | Kučera, R |
| collection | OXFORD |
| description | We report the catalytic asymmetric synthesis of Tafluprost (1), a prostaglandin analogue. This synthesis demonstrates a new approach to prostaglandins involving symmetrization and desymmetrization of a racemic precursor to control the absolute and relative stereochemistry of the cyclopentyl core. Key steps include a diastereo- and enantioselective Rh-catalyzed Suzuki–Miyaura reaction of a racemic bicyclic allyl chloride and an alkenyl boronic acid and a regio- and diastereoselective Pd-catalyzed Tsuji–Trost reaction with an enolate surrogate.
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| first_indexed | 2024-03-06T20:57:15Z |
| format | Journal article |
| id | oxford-uuid:39ab9f09-3ddc-4774-a2a6-7d00185ed7a1 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-06T20:57:15Z |
| publishDate | 2020 |
| publisher | American Chemical Society |
| record_format | dspace |
| spelling | oxford-uuid:39ab9f09-3ddc-4774-a2a6-7d00185ed7a12022-03-26T13:57:02ZAn asymmetric Suzuki-Miyaura approach to prostaglandins: Synthesis of TafluprostJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:39ab9f09-3ddc-4774-a2a6-7d00185ed7a1EnglishSymplectic ElementsAmerican Chemical Society2020Kučera, RGoetzke, FWFletcher, SPWe report the catalytic asymmetric synthesis of Tafluprost (1), a prostaglandin analogue. This synthesis demonstrates a new approach to prostaglandins involving symmetrization and desymmetrization of a racemic precursor to control the absolute and relative stereochemistry of the cyclopentyl core. Key steps include a diastereo- and enantioselective Rh-catalyzed Suzuki–Miyaura reaction of a racemic bicyclic allyl chloride and an alkenyl boronic acid and a regio- and diastereoselective Pd-catalyzed Tsuji–Trost reaction with an enolate surrogate. |
| spellingShingle | Kučera, R Goetzke, FW Fletcher, SP An asymmetric Suzuki-Miyaura approach to prostaglandins: Synthesis of Tafluprost |
| title | An asymmetric Suzuki-Miyaura approach to prostaglandins: Synthesis of Tafluprost |
| title_full | An asymmetric Suzuki-Miyaura approach to prostaglandins: Synthesis of Tafluprost |
| title_fullStr | An asymmetric Suzuki-Miyaura approach to prostaglandins: Synthesis of Tafluprost |
| title_full_unstemmed | An asymmetric Suzuki-Miyaura approach to prostaglandins: Synthesis of Tafluprost |
| title_short | An asymmetric Suzuki-Miyaura approach to prostaglandins: Synthesis of Tafluprost |
| title_sort | asymmetric suzuki miyaura approach to prostaglandins synthesis of tafluprost |
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