Issue 8, 2011
From the journal:

Chemical Science

Quasi-biomimetic ring contraction promoted by a cysteine-based nucleophile: Total synthesis of Sch-642305, some analogs and their putative anti-HIV activities†

Alpay Dermenci,a   Philipp S. Selig,a   Robert A. Domaoal,b   Krasimir A. Spasov,b   Karen S. Anderson*b  and  Scott J. Miller*a  

* Corresponding authors

a Department of Chemistry, Yale University, 225 Prospect Street, New Haven, USA
E-mail: scott.miller@yale.edu
Fax: (+1) 203-496-4900

b Department of Pharmacology, Yale University School of Medicine, 333 Cedar Street, New Haven, USA
E-mail: karen.anderson@yale.edu
Fax: (+1) 203-785-7670

Abstract

Cysteine plays a number of important functional and structural roles in nature, often in the realm of catalysis. Herein, we present an example of a cysteine-promoted Rauhut-Currier reaction for a potentially biomimetic synthesis of Sch-642305 and related analogs. In this key step of the synthesis we discuss interesting new discoveries and the importance of substrate-catalyst recognition, as well as cysteine's structural features. Also, we investigate the activity of Sch-642305 and four analogs in HIV-infected T-cells.

Graphical abstract: Quasi-biomimetic ring contraction promoted by a cysteine-based nucleophile: Total synthesis of Sch-642305, some analogs and their putative anti-HIV activities

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Article information

DOI
https://doi.org/10.1039/C1SC00221J
Article type
Edge Article
Submitted
06 Apr 2011
Accepted
23 May 2011
First published
20 Jun 2011

Chem. Sci., 2011,2, 1568-1572

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Quasi-biomimetic ring contraction promoted by a cysteine-based nucleophile: Total synthesis of Sch-642305, some analogs and their putative anti-HIV activities

A. Dermenci, P. S. Selig, R. A. Domaoal, K. A. Spasov, K. S. Anderson and S. J. Miller, Chem. Sci., 2011, 2, 1568 DOI: 10.1039/C1SC00221J

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