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Directed synthesis of all four pure stereoisomers of the N,C-coupled naphthylisoquinoline alkaloid ancistrocladinium A

Abstract:

The first preparation of the N,C-coupled naphthylisoquinoline alkaloid ancistrocladinium A and its likewise naturally occurring minor atropisomer, in an atropisomerically pure form, is described. The synthesis succeeded by resolution of the already rotationally hindered, and thus atropo-diastereomeric acetamide precursors, which were then, without major loss of stereochemical information, cyclized to the respective target molecules. The strategy was applied to the first synthesis of the regio...

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Publication status:
Published
Peer review status:
Peer reviewed

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Publisher copy:
10.1021/acs.orglett.6b03480

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Institution:
University of Oxford
Division:
Medical Sciences Division
Department:
NDM; Target Discovery Institute
Role:
Author
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Grant:
SFB 630: Agents against Infectious Diseases
Publisher:
American Chemical Society Publisher's website
Journal:
Organic Letters Journal website
Volume:
18
Issue:
24
Pages:
6508-6511
Publication date:
2016-12-01
Acceptance date:
2016-12-01
DOI:
EISSN:
1523-7052
ISSN:
1523-7060
Pubs id:
pubs:863175
URN:
uri:5a532ddb-e85f-4bc8-bc59-cb3e79d8eb93
UUID:
uuid:5a532ddb-e85f-4bc8-bc59-cb3e79d8eb93
Local pid:
pubs:863175
Language:
English

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