Tetrahedron

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

KA Oppong, T Hudlicky, F Yan, C York, BV Nguyen

Index: Oppong, Kofi A.; Hudlicky, Tomas; Yan, Fengyang; York, Chentao; Nguyen, Ba V. Tetrahedron, 1999 , vol. 55, # 10 p. 2875 - 2880

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Citation Number: 12

Abstract

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 SN2 displacement of triflates 7, 11. Fluorine was selectively introduced via trans-diaxial epoxide opening with tetrabutylphosphonium fluoride dihydrofluoride (TBPF-DF).

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