Next Article in Journal
Development of Diversified Methods for Chemical Modification of the 5,6-Double Bond of Uracil Derivatives Depending on Active Methylene Compounds
Next Article in Special Issue
Chitosan Based Heterogeneous Catalyses: Chitosan-Grafted-Poly(4-Vinylpyridne) as an Efficient Catalyst for Michael Additions and Alkylpyridazinyl Carbonitrile Oxidation
Previous Article in Journal
Variation in Minerals, Phenolics and Antioxidant Activity of Peel and Pulp of Different Varieties of Peach (Prunus persica L.) Fruit from Pakistan
Previous Article in Special Issue
H2TPP Organocatalysis in Mild and Highly Regioselective Ring Opening of Epoxides to Halo Alcohols by Means of Halogen Elements
Article Menu

Article Versions

Export Article

Open AccessArticle
Molecules 2012, 17(6), 6507-6518; doi:10.3390/molecules17066507

Asymmetric Synthesis of the Carbon-14-Labeled Selective Glucocorticoid Receptor Modulator using Cinchona Alkaloid Catalyzed Addition of 6-Bromoindole to Ethyl Trifluoropyruvate

Drug Research Division, Dainippon Sumitomo Pharma Co., Ltd., 33-94 Enoki, Suita, Osaka 564-0053, Japan
*
Author to whom correspondence should be addressed.
Received: 27 April 2012 / Revised: 18 May 2012 / Accepted: 21 May 2012 / Published: 30 May 2012
(This article belongs to the Special Issue Organocatalysis)
Download PDF [274 KB, uploaded 18 June 2014]   |  

Abstract

We describe in this study the asymmetric synthesis of radioisotope (RI)-labeled selective glucocorticoid receptor modulator. This synthesis is based on optimization of the cinchona alkaloid catalyzed addition of 6-bromoindole to ethyl trifluoropyruvate and Negishi coupling of zinc cyanide to the 6-bromoindole moiety. [14C] Labeled (−)-{4-[(1-{2-[6-cyano-1-(cyclohexylmethyl)-1H-indol-3-yl]-3,3,3-trifluoro-2-hydroxypropyl}piperidin-4-yl)oxy]-3-methoxyphenyl}acetic acid (−)-1 was synthesized successfully with high enantioselectivity ( > 99% ee) and sufficient radiochemical purity.
Keywords: organocatalyst; cinchona alkaloid; asymmetric synthesis; radioisotope labeled compound organocatalyst; cinchona alkaloid; asymmetric synthesis; radioisotope labeled compound
Figures

This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

MDPI and ACS Style

Sumiyoshi, T.; Urabe, D.; Tojo, K.; Sakamoto, M.; Niidome, K.; Tsuboya, N.; Nakajima, T.; Tobe, M. Asymmetric Synthesis of the Carbon-14-Labeled Selective Glucocorticoid Receptor Modulator using Cinchona Alkaloid Catalyzed Addition of 6-Bromoindole to Ethyl Trifluoropyruvate. Molecules 2012, 17, 6507-6518.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top