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Expeditious and divergent total syntheses of aspidosperma alkaloids exploiting iridium(I)-catalyzed generation of reactive enamine intermediates

Abstract:

A new approach for the divergent total syntheses of (±)-vincaminorine, (±)-N-methylquebrachamine, (±)-quebrachamine, (±)-minovine and (±)-vincadifformine, each in less than 10 linear steps starting from a single δ-lactam building block, is reported. Key to our route design is the late-stage generation of reactive enamine functionality from stable indole-linked δ-lactams via a highly chemoselective iridium(I)-catalyzed reduction. The efficiently formed secodine intermediates subsequently under...

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Publication status:
Published
Peer review status:
Peer reviewed

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Files:
Publisher copy:
10.1002/anie.201605503

Authors


More by this author
Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
More by this author
Institution:
University of Oxford
Oxford college:
Wadham College
Role:
Author
Publisher:
Wiley Publisher's website
Journal:
Angewandte Chemie International Edition Journal website
Volume:
55
Issue:
43
Pages:
13436-13440
Publication date:
2016-09-23
DOI:
EISSN:
1521-3773
ISSN:
1433-7851
Pmid:
27659476
Source identifiers:
648254
Language:
English
Keywords:
Pubs id:
pubs:648254
UUID:
uuid:ccb730ec-767a-4d5f-9922-b2a9ce579520
Local pid:
pubs:648254
Deposit date:
2016-12-02

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