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Asymmetric synthesis of the allocolchicinoid natural product N-acetylcolchinol methyl ether (suhailamine), solid state and solution phase conformational analysis

Abstract:

An asymmetric synthesis of the allocolchicinoid N-acetylcolchinol methyl ether (NCME) from 3-methoxybenzaldehyde is reported. Comparison of 1H and 13C NMR spectroscopic data obtained for this sample of NCME provide further evidence for the assertion that this compound is congruous with the natural product that has been dubbed suhailamine, establishing NCME as a naturally-occurring allocolchicinoid. The single crystal X-ray diffraction structure of NCME is also reported for the first time, rev...

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Publication status:
Published
Peer review status:
Peer reviewed

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Publisher copy:
10.1016/j.tet.2019.130694

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Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Oxford college:
St Catherine's College
Role:
Author
Publisher:
Elsevier
Journal:
Tetrahedron More from this journal
Volume:
75
Issue:
49
Article number:
130694
Publication date:
2019-10-18
Acceptance date:
2019-10-14
DOI:
EISSN:
1464-5416
ISSN:
0040-4020
Language:
English
Keywords:
Pubs id:
pubs:1071962
UUID:
uuid:295c37b4-e5e2-4c7f-9101-4f86750b785b
Local pid:
pubs:1071962
Source identifiers:
1071962
Deposit date:
2019-11-17

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