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Total synthesis and structure confirmation of elatenyne: success of computational methods for NMR prediction with highly flexible diastereomers.

Abstract:

Elatenyne is a small dibrominated natural product first isolated from Laurencia elata. The structure of elatenyne was originally assigned as a pyrano[3,2-b]pyran on the basis of NMR methods. Total synthesis of the originally proposed pyrano[3,2-b]pyran structure of elatenyne led to the gross structure of the natural product being reassigned as a 2,2'-bifuranyl. The full stereostructure of this highly flexible small molecule was subsequently predicted by Boltzmann-weighted DFT calculations of ...

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Publication status:
Published

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Publisher copy:
10.1021/ja304554e

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
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Journal:
Journal of the American Chemical Society
Volume:
134
Issue:
28
Pages:
11781-11790
Publication date:
2012-07-05
DOI:
EISSN:
1520-5126
ISSN:
0002-7863
URN:
uuid:9fd69ff6-c839-4bf1-8a34-6ef9cee17f8c
Source identifiers:
341079
Local pid:
pubs:341079

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