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

✍ Scribed by Kofi A. Oppong; Tomas Hudlicky; Fengyang Yan; Chentao York; Ba V. Nguyen

Publisher: Elsevier Science
Year: 1999
Tongue: French
Weight: 470 KB
Volume: 55
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(99)00080-0

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✦ Synopsis

Both enantiomers of dideoxyfluoroamino inositols (+)-9 and (-)-9 were synthesized from bromocyclohexadiene cLv-diol I obtained by microbial oxidation of bromobenzene with toluene dioxygenase. Selective introduction of the amino group was achieved through S~2 displacement of trifates 7, l l. Fluorine was selectively introduced via trans-diaxial epoxide opening with tetrabutylphosphonium fuoride dihydrofluoride (TBPF-DF).

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