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Asymmetric syntheses of (-)-1-deoxymannojirimycin and (+)-1-deoxyallonojirimycin via a ring-expansion approach.

Abstract:
The asymmetric syntheses of (-)-1-deoxymannojirimycin and (+)-1-deoxyallonojirimycin are described herein. The ring-closing iodoamination of two epimeric bishomoallylic amines to give the corresponding 5-iodomethylpyrrolidines was followed by in situ ring-expansion to give two diastereoisomerically pure (>99:1 dr) cyclic carbonates. Subsequent deprotection gave (-)-1-deoxymannojirimycin and (+)-1-deoxyallonojirimycin as single diastereoisomers in 7.4 and 3.3% overall yield, respectively, from commercially available starting materials.
Publication status:
Published

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Publisher copy:
10.1021/ol400735z

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
More by this author
Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
More by this author
Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
Journal:
Organic letters
Volume:
15
Issue:
8
Pages:
2042-2045
Publication date:
2013-04-05
DOI:
EISSN:
1523-7052
ISSN:
1523-7060
URN:
uuid:8f73d27b-7090-40ac-bd02-d0a438398aac
Source identifiers:
394908
Local pid:
pubs:394908

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