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

Demir, AYHAN; Aksoy-Cam, H; Camkerten, N; Hamamci, HALUK; Doganel, F

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, Scopus, TRDizin)

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.