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, sa.2, ss.141-146, 2000 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 24 Sayı: 2
  • Basım Tarihi: 2000
  • Dergi Adı: TURKISH JOURNAL OF CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, TR DİZİN (ULAKBİM)
  • Sayfa Sayıları: ss.141-146
  • Orta Doğu Teknik Üniversitesi Adresli: Evet

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.