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

Demir A., Hamamci H., Doganel F., Ozgul E.

JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, vol.9, pp.157-161, 2000 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 9
  • Publication Date: 2000
  • Doi Number: 10.1016/s1381-1177(99)00092-2
  • Journal Name: JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.157-161
  • Keywords: biotransformation, 1-amino-2-indanol, Rhizopus oryzae, enantioselective hydrolysis, enantioselective reduction, BETA-AMINO ALCOHOLS, ENANTIOSELECTIVE REDUCTION, KETONES, OXIDATION, ETHERS
  • Middle East Technical University Affiliated: Yes

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. (C) 2000 Elsevier Science B.V. All lights reserved.