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

Metadata

Show full item record

This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Item Usage Stats

49
views

0
downloads

(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

Suggestions

OpenMETU
Core

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...
The facile synthesis of cyclopentanoid antibiotic kjellmanianone Demir, Ayhan Sıtkı; Tanyeli, Cihangir; Gulbeyaz, V; Akgul, H (1996-01-01) The synthesis of cyclopentanoid antibiotic Kjellmanianone is described in this study. The C-acylation of lithium enolates of 3-Methoxycyclopentenone by N-carbomethoxyimidazole or methylcyanoformate beta-ketoester, which when oxidized with Mn(III) acetate produces kjellmanianone in good yield.
Development of a novel zebrafish xenograft model in ache mutants using liver cancer cell lines Avci, M. Ender; Keskus, Ayse Gokce; Targen, Seniye; Isilak, M. Efe; Ozturk, Mehmet; Atalay, Rengül; ADAMS, MİCHELLE; KONU KARAKAYALI, ÖZLEN (2018-01-25) Acetylcholinesterase (AChE), an enzyme responsible for degradation of acetylcholine, has been identified as a prognostic marker in liver cancer. Although in vivo Ache tumorigenicity assays in mouse are present, no established liver cancer xenograft model in zebrafish using an ache mutant background exists. Herein, we developed an embryonic zebrafish xenograft model using epithelial (Hep3B) and mesenchymal (SKHep1) liver cancer cell lines in wild-type and achesb55 sibling mutant larvae after characterization...
Investigation of the therapeutic effect of sodium butyrate in Caco-2 colon cancer cell line by using ATR-FTIR spectroscopy Çelik, Buket; Bek, Alpan; Özek, Nihal Şimşek; Department of Micro and Nanotechnology (2018) Sodium butyrate (NaBt), as one of the HDACi, has been demonstrated that it induces apoptosis, cell cycle arrest, the inhibition of angiogenesis, metastasis and gene expression changes. To date, there are several studies perfomed to investigate its therapeutic effect; however, theexact mechanism at molecular level is not clear yet. Therefore, the current thesis was aimed to clarify the action/theurapeutic potential mechanisms of sodium butyrate in Caco2 colon cancer cell line at molecular level using ATR-FTI...
The Preparation of azido amino acids and the application of native chemical ligation in the synthesis of chlorotoxin Karaca, Ulvi Oral; Özçubukçu, Salih; Department of Chemistry (2014) In this project, the pharmaceutically and biologically important peptide, chlorotoxin (CLTX), and some derivatives of CLTX containing azido amino acids was synthesized by using solid phase peptide synthesis (SPPS) based on 9-fluorenylmethyloxycarbonyl (Fmoc) chemistry strategy and native chemical ligation. The native chemical ligation provides more efficient than only SPPS. Directly synthesis of CLTX by SPPS has very low yield, by using native chemical ligation, the yield is aimed much higher. The CLTX can ...

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.