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Synthesis and glycosidase inhibition of broussonetine M and its analogues

Abstract:

Cross-metathesis (CM) and Keck asymmetric allylation, which allows access to defined stereochemistry of a remote side chain hydroxyl group, are the key steps in a versatile synthesis of broussonetine M (3) from the d-arabinose-derived cyclic nitrone 14. By a similar strategy, ent-broussonetine M (ent-3) and six other stereoisomers have been synthesized, respectively, starting from l-arabino-nitrone (ent-14), l-lyxo-nitrone (ent-3-epi-14), and l-xylo-nitrone (2-epi-14) in five steps, in 26%–31...

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Publication status:
Published
Peer review status:
Peer reviewed

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Publisher copy:
10.3390/molecules24203712

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Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
Publisher:
MDPI Publisher's website
Journal:
Molecules Journal website
Volume:
24
Issue:
20
Article number:
3712
Publication date:
2019-10-15
Acceptance date:
2019-10-14
DOI:
EISSN:
1420-3049
ISSN:
1420-3049
Language:
English
Keywords:
Pubs id:
pubs:1065729
UUID:
uuid:23d9a2ca-d3bd-4e27-ad50-e958be7c5924
Local pid:
pubs:1065729
Source identifiers:
1065729
Deposit date:
2019-10-27

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