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A cascade strategy enables a total synthesis of (-)-gephyrotoxin.

Abstract:

A concise and efficient synthesis of (-)-gephyrotoxin from L-pyroglutaminol has been realized. The key step in this approach is a diastereoselective intramolecular enamine/Michael cascade reaction that forms two rings and two stereocenters and generates a stable tricyclic iminium cation. A hydroxy-directed reduction of this intermediate plays a key role in establishing the required cis-decahydroquinoline ring system, enabling the total synthesis of (-)-gephyrotoxin in nine steps and 14% overa...

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Publication status:
Published
Peer review status:
Peer reviewed
Version:
Accepted manuscript

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Publisher copy:
10.1002/anie.201409038

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Wallace, S More by this author
More by this author
Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Publisher:
Wiley Publisher's website
Journal:
Angewandte Chemie (International ed. in English) Journal website
Volume:
53
Issue:
50
Pages:
13826-13829
Publication date:
2014-12-05
DOI:
EISSN:
1521-3773
ISSN:
1433-7851
URN:
uuid:22c016c3-8aae-488e-ae33-b597e65ca19a
Source identifiers:
487220
Local pid:
pubs:487220
Language:
English
Keywords:

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