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

(1S,2R)-l-amino-2-indanol, a key component of an HIV protease inhibitor is synthesized in four steps starting from indanone. The Mn(OAC)s mediated acetoxylation of indanone followed by fungus catalyzed hydrolysis of acetoxyindanone furnished optically pure a-hydroxy indanone. Formation and enantiose...

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Bibliographic Details
Published in:Turkish journal of chemistry 2000, Vol.24 (2), p.141-146
Main Authors: CAMKERTEN, Nurettin, CAM, Hilal,Aksoy, HAMAMCI, Haluk, DOĞANEL, Fatoş, DEMİR, Ayhan S
Format: Article
Language:English
Subjects:
1-amino-2-indanol
HIV protease inhibitor
HIV proteaz inhibitör
İmin indirgenmesi
Imine reduction
Indinavir
Mangan
manganese
Oksitlenme
Organic Chemistry
Organik Kimya
oxidation
Sentez
synthesis
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Summary:(1S,2R)-l-amino-2-indanol, a key component of an HIV protease inhibitor is synthesized in four steps starting from indanone. The Mn(OAC)s mediated acetoxylation of indanone followed by fungus catalyzed hydrolysis of acetoxyindanone furnished optically pure a-hydroxy indanone. Formation and enantioselective reduction of oxime ether of 2-hydroxyindanone afforded (1S, 2R)-l-amino-2-indanol in 97% cis selectivity.
ISSN:1300-0527
1303-6130