Enantioselective Synthesis of (-)-Conduramine C-1 and Aminobromocyclitol Derivatives
Allemann, S.; Vogel, P.
1994

Abstract

(1S,2R,6R,7R)-4-Phenyl-3,10-dioxa-5-azatricyclo[5.2.1.0(2,6)]dec-4-en-9- one ((+)-5) obtained in 6 steps from the Diels-Alder adduct of furan to 1-cyanovinyl (1S)-camphanate ((+)-3) was reduced to the corresponding endo-alcohol (-)-6 the treatment of which with HBr/AcOH provided (-)-(3aS,4S,6R,7S,7aR)-4 beta-bromo-3a beta,4,5,6,7,7a beta-hexahydro-2-phenyl-1,3-benzoxazole-6 beta,7 alpha-diyl diacetale ((-)-17). Elimination of HBr with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and acidic hydrolysis furnished (-)-(1R,2S,3R,4R)-4-aminocycrohex-5-ene-1,2,3-triol(= (-)-conduramine C-1; (-)-1).

Details

Title Enantioselective Synthesis of (-)-Conduramine C-1 and Aminobromocyclitol Derivatives
Author(s) Allemann, S. ; Vogel, P.
Published in Helvetica Chimica Acta
Volume 77
Issue 1
Pages 1-9
Date 1994
ISSN 0018-019X
Keywords
Note Univ lausanne,chim sect,ch-1005 lausanne,switzerland.
DOI https://doi.org/10.1002/hlca.19940770103
Laboratories LGSA
Record Appears in Scientific production and competences > SB - School of Basic Sciences > SB Archives > LGSA - Laboratory of Glycochemistry and Asymmetric Synthesis
Peer-reviewed publications
Work produced at EPFL
Journal Articles
Published
Record creation date 2005-11-09

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