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Structural revision of the Hancock alkaloid (-)-galipeine

Abstract:

The 1H and 13C NMR data of synthetic samples of (S)-N(1)-methyl-2-[2'-(3″-hydroxy-4″-methoxyphenyl)ethyl]-1,2,3,4-tetrahydroquinoline, the originally proposed structure of the Hancock alkaloid (-)-galipeine, do not match those of the natural product. Herein, the preparation of the regioisomer (S)-N(1)-methyl-2-[2'-(3″-methoxy-4″-hydroxyphenyl)ethyl]-1,2,3,4-tetrahydroquinoline is reported, the 1H and 13C NMR data of which are in excellent agreement with those of (-)-galipeine. Comparison of s...

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

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Publisher copy:
10.1021/acs.joc.7b01720

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Department:
Magdalen College
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Department:
Oxford, MPLS, Chemistry, Organic Chemistry
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Department:
Oxford, MPLS, Chemistry, Organic Chemistry
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Department:
Oxford, MPLS, Chemistry, Organic Chemistry
More by this author
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Publisher:
American Chemical Society Publisher's website
Journal:
Journal of Organic Chemistry Journal website
Volume:
82
Issue:
19
Pages:
10673–10679
Publication date:
2017-08-15
Acceptance date:
2017-08-15
DOI:
EISSN:
1520-6904
ISSN:
0022-3263
Pubs id:
pubs:726246
URN:
uri:c60be976-e263-46fb-8911-b39fabace665
UUID:
uuid:c60be976-e263-46fb-8911-b39fabace665
Local pid:
pubs:726246
Language:
English

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