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


Demir A. , Aksoy-Cam H., Camkerten N., Hamamci H. , Doganel F.

TURKISH JOURNAL OF CHEMISTRY, cilt.24, ss.141-146, 2000 (SCI İndekslerine Giren Dergi) identifier identifier

  • Cilt numarası: 24 Konu: 2
  • Basım Tarihi: 2000
  • Dergi Adı: TURKISH JOURNAL OF CHEMISTRY
  • Sayfa Sayıları: ss.141-146

Özet

(1S,2R)-1-amino-2-indanol, a key component of an HIV protease inhibitor is synthesized in four steps starting from indanone. The Mn(OAC)(3) mediated acetoxylation of indanone followed by fungus catalyzed hydrolysis of acetoxyindanone furnished optically pure alpha-hydroxy indanone. Formation and enantioselective reduction of oxime ether of 2-hydroxyindanone afforded (1S, 2R)-1-amino-2-indanol in 97% cis selectivity.