Chemoenzymatic synthesis of (1<i>S</i>,2<i>R</i>)-1-amino-2-indanol, a key intermediate of HIV protease inhibitor, indinavir期刊界 All Journals 搜尽天下杂志传播学术成果专业期刊搜索期刊信息化学术搜索

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

Authors:	Ayhan S. Demir Haluk Hamamci Fatos Doganel Emine Ozgul

Affiliation:	^a Department of Chemistry, Middle East Technical University, 06531 Ankara, Turkey ^b Department of Biotechnology, Middle East Technical University, 06531 Ankara, Turkey ^c Department of Food Engineering, Middle East Technical University, 06531 Ankara, Turkey

Abstract:	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.

Keywords:	Biotransformation 1-Amino-2-indanol Rhizopus oryzae Enantioselective hydrolysis Enantioselective reduction
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