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Hydroxylated C-branched pyrrolidines, C-branched prolines and C-branched piperidines from a 2-C-methyl sugar lactone; efficient azide displacement of a tertiary triflate with inversion of configuration

Abstract:
The versatility of 3,4-O-isopropylidene-2-C-methyl-d-arabinonolactone [from d-erythronolactone] as a chiron for complex piperidines and pyrrolidines is illustrated by the synthesis of (2R,3S,4S)- and (2R,3S,4R)-dihydroxy-2-C-methyl prolines, 1,4-dideoxy-1,4-imino-4-C-methyl-l-ribitol and 1,4-dideoxy-1,4-imino-4-C-methyl-l-arabinitol, and isofagomine derivatives; the enantiomeric series is equally accessible from l-erythronolactone. © 2008 Elsevier Ltd. All rights reserved.
Publication status:
Published

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
Journal:
TETRAHEDRON LETTERS
Volume:
49
Issue:
48
Pages:
6812-6815
Publication date:
2008-11-24
DOI:
ISSN:
0040-4039
URN:
uuid:488d33ec-235e-4faa-867f-584e8d9bb2af
Source identifiers:
40966
Local pid:
pubs:40966
Language:
English

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