Chemoenzymatic enantiodivergent synthesis of 1,2-dideoxy-2-amino-1-fluoro- allo-inositol

Both enantiomers of dideoxyfluoroamino inositols (+)-9 and (−)-9 were synthesized from bromocyclohexadiene cis-diol 1 obtained by microbial oxidation of bromobenzene with toluene dioxygenase. Selective introduction of the amino group was achieved through S N2 displacement of triflates 7, 11. Fluorin...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron 1999-03, Vol.55 (10), p.2875-2880
Main Authors: Oppong, Kofi A., Hudlicky, Tomas, Yan, Fengyang, York, Chentao, Nguyen, Ba V.
Format: Article
Language:English
Subjects:
Biooxidation
Enantioselectivity
Fluoroamino Inositols
Toluene dioxygenase
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Both enantiomers of dideoxyfluoroamino inositols (+)-9 and (−)-9 were synthesized from bromocyclohexadiene cis-diol 1 obtained by microbial oxidation of bromobenzene with toluene dioxygenase. Selective introduction of the amino group was achieved through S N2 displacement of triflates 7, 11. Fluorine was selectively introduced via trans-diaxial epoxide opening with tetrabutylphosphonium fluoride dihydrofluoride (TBPF-DF). The enantiodivergent synthesis of dideoxyfluoroamino inositols (+)-9 and (−)-9 from the microbial metabolite bromocyclohexadiene cis-diol is described.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(99)00080-0