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Issue 8, 2011
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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

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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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Publication details

The article was received on 06 Apr 2011, accepted on 23 May 2011 and first published on 20 Jun 2011


Article type: Edge Article
DOI: 10.1039/C1SC00221J
Citation: 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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