Journal article icon

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

Actions


Access Document


Files:
Publisher copy:
10.1021/acs.orglett.0c00745

Authors


More by this author
Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Oxford college:
New College
Role:
Author
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:
1523-7060
Language:
English
Keywords:
Pubs id:
1094578
Local pid:
pubs:1094578
Deposit date:
2020-03-17

Terms of use


Views and Downloads






If you are the owner of this record, you can report an update to it here: Report update to this record

TO TOP