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Hanessian-Hullar reaction in the synthesis of highly substituted trans-3,4-dihydroxypyrrolidines: rhamnulose iminosugar mimics inhibit alpha-glucosidase

Abstract:

The key step in the syntheses of highly substituted trans-3,4-dihydroxypyrrolidines is introduction of bromide by stereospecific and regiospecific Hanessian-Hullar reactions; benzylidene lactones of l-rhamnonolactone and 6-deoxy-this should be small unnpercase d not l why can I not correct this-gulonolactone allow introduction of N at C2 with inversion or retention of configuration. Initially a protecting group, the benzylidene acetal then provides a bromide at C5 to allow formation of the py...

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Publication status:
Published
Peer review status:
Peer reviewed

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Publisher copy:
10.1016/j.tet.2019.130758

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Institution:
University of Oxford
Division:
MSD
Department:
Biochemistry
Role:
Author
More by this author
Institution:
University of Oxford
Division:
MSD
Department:
Biochemistry
Role:
Author
ORCID:
0000-0002-4853-2773
Publisher:
Elsevier
Journal:
Tetrahedron More from this journal
Volume:
76
Issue:
1
Article number:
130758
Publication date:
2019-11-06
Acceptance date:
2019-10-31
DOI:
ISSN:
0040-4020
Language:
English
Keywords:
Pubs id:
pubs:1069071
UUID:
uuid:13916d00-f78c-4953-91b8-36c9e2081c63
Local pid:
pubs:1069071
Source identifiers:
1069071
Deposit date:
2019-11-01

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