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  4. Enantioselective Synthesis of (-)-Conduramine C-1 and Aminobromocyclitol Derivatives
 
research article

Enantioselective Synthesis of (-)-Conduramine C-1 and Aminobromocyclitol Derivatives

Allemann, S.
•
Vogel, P.  
1994
Helvetica Chimica Acta

(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
  • Metrics
Type
research article
DOI
10.1002/hlca.19940770103
Author(s)
Allemann, S.
Vogel, P.  
Date Issued

1994

Published in
Helvetica Chimica Acta
Volume

77

Issue

1

Start page

1

End page

9

Subjects

Pure 7-oxabicyclo<2.2.1>hept-5-en-2-yl derivatives

•

diels-alder

•

reactions

•

nitroso-compounds

•

diene synthesis

•

pseudo-sugars

•

polyhydroxyamino compounds

•

microbial oxidation

•

cyclitol reactions

•

naked sugars

•

enzymatic asymmetrization

Note

Univ lausanne,chim sect,ch-1005 lausanne,switzerland.

Editorial or Peer reviewed

REVIEWED

Written at

EPFL

EPFL units
LGSA  
Available on Infoscience
November 9, 2005
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/219683
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