Chemoenzymatic synthesis of (1S,2R)-1-amino-2-indanol, a key intermediate of HIV protease inhibitor, indinavir

被引：19

作者：

Demir, AS ^{[1
]}

Hamamci, H

Doganel, F

Ozgul, E

机构：

[1] Middle E Tech Univ, Dept Chem, TR-06531 Ankara, Turkey

[2] Middle E Tech Univ, Dept Biotechnol, TR-06531 Ankara, Turkey

[3] Middle E Tech Univ, Dept Food Engn, TR-06531 Ankara, Turkey

来源：

JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC | 2000年 / 9卷 / 4-6期

关键词：

biotransformation; 1-amino-2-indanol; Rhizopus oryzae; enantioselective hydrolysis; enantioselective reduction;

D O I：

10.1016/S1381-1177(99)00092-2

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The synthesis of (1S,2R)-1-amino-2-indanol, a key component of HIV protease inhibitor is accomplished in four steps starting from indanone efficiently and with high levels of diastereo- and enantioselectivity. The starting material is converted into 2-acetoxy-1-indanone involving Manganese (III) acetate oxidation. The 2-acetoxyketone is hydrolyzed to 2-hydroxy-1-indanone enantioselectively using Rhizopus oryzae. Selective reduction of 2-hydroxyoxime derivative, derived from the 2-hydroxyketone, gives the amino alcohol up to 98% diastereo- and enantioselectivity. (C) 2000 Elsevier Science B.V. All lights reserved.

引用

页码：157 / 161

页数：5

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