Journal article
An asymmetric Suzuki-Miyaura approach to prostaglandins: Synthesis of Tafluprost
- Abstract:
- 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.
- Publication status:
- Published
- Peer review status:
- Peer reviewed
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(Accepted manuscript, 416.9KB)
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- Publisher copy:
- 10.1021/acs.orglett.0c00745
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Authors
Bibliographic Details
- Publisher:
- American Chemical Society Publisher's website
- Journal:
- Organic Letters Journal website
- Volume:
- 22
- Issue:
- 8
- Pages:
- 2991-2994
- Publication date:
- 2020-03-27
- Acceptance date:
- 2020-03-16
- DOI:
- EISSN:
-
1523-7052
- ISSN:
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1523-7060
Item Description
- Language:
- English
- Keywords:
- Pubs id:
-
1094578
- Local pid:
- pubs:1094578
- Deposit date:
- 2020-03-17
Terms of use
- Copyright holder:
- American Chemical Society
- Copyright date:
- 2020
- Rights statement:
- Copyright © 2020 American Chemical Society
- Notes:
-
This is the accepted manuscript version of the article. The final version is available from American Chemical Society at https://doi.org/10.1021/acs.orglett.0c00745
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