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Synthesis of the naringinase inhibitors L-swainsonine and related 6-C-methyl-L-swainsonine analogues: (6R)-C-methyl-L-swainsonine is a more potent inhibitor of L-rhamnosidase by an order of magnitude than L-swainsonine

Abstract:

Efficient syntheses are reported of the α-l-rhamnosidase inhibitors l-swainsonine [(1R,2S,8S,8aS)-octahydroindolizine-1,2,8-triol], (6R)-C-methyl-l-swainsonine (1R,2S,6R,8S,8aS)-6-methyloctahydro-indolizine-1,2,8-triol, (6S)-C-methyl-l-swainsonine (1R,2S,6S,8S,8aS)-6-methyloctahydro-indolizine-1,2,8-triol and related 6-C-methyl hydroxycastanospermines [(1R,2S,6R,7R,8R,8aR)-6-methyl-octahydroindolizine-1,2,6,7,8-pentaol and (1R,2S,6S,8S,8aS)-6-methyloctahydro-indolizine-1,2,8-triol]. (6R)-C-Me...

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Publication status:
Published

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Institution:
University of Oxford
Department:
Oxford, MSD, Biochemistry
Role:
Author
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Journal:
TETRAHEDRON LETTERS
Volume:
49
Issue:
1
Pages:
179-184
Publication date:
2008-01-01
DOI:
ISSN:
0040-4039
URN:
uuid:dfa61298-ac31-44bb-ae3f-b6115322becc
Source identifiers:
40641
Local pid:
pubs:40641
Language:
English

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