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

被引：12
|
作者：
Oppong, KA [1 ]
Hudlicky, T [1 ]
Yan, FY [1 ]
York, CT [1 ]
Nguyen, BV [1 ]
机构：
[1] Univ Florida, Dept Chem, Gainesville, FL 32611 USA
来源：
TETRAHEDRON | 1999年 / 55卷 / 10期
基金：
美国国家科学基金会;
关键词：
biooxidation; enantioselectivity; fluoroamino inositols; toluene dioxygenase;
D O I：
10.1016/S0040-4020(99)00080-0
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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(N)2 displacement of triflates 7, 11. Fluorine was selectively introduced via trans-diaxial epoxide opening with tetrabutylphosphonium fluoride dihydrofluoride (TBPF-DF). (C) 1999 Elsevier Science Ltd. All rights reserved.
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页码：2875 / 2880
页数：6
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