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

Date

2000-01-01

Author

Demir, Ayhan Sıtkı
Aksoy-Cam, H
Camkerten, N
Hamamcı, Haluk
Doganel, F

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(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.

Subject Keywords

Manganese(III) oxidation, Imine reduction, Enantioselective hydrolysis, 1-amino-2-indanol

URI

https://hdl.handle.net/11511/54811

Journal

TURKISH JOURNAL OF CHEMISTRY

Collections

Department of Chemistry, Article

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Chemoenzymatic synthesis of (1S,2R)-1-amino-2-indanol, a key intermediate of HIV protease inhibitor, indinavir Demir, AS; Hamamcı, Haluk; Doganel, F; Ozgul, E (2000-04-21) 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 am...
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Citation Formats

A. S. Demir, H. Aksoy-Cam, N. Camkerten, H. Hamamcı, and F. Doganel, “An efficient synthesis of (1S, 2R)-1-amino-2-indanol, a key intermediate of HIV protease inhibitor, indinavir,” TURKISH JOURNAL OF CHEMISTRY, pp. 141–146, 2000, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/54811.