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. 2011 Aug 1;2(8):10.1039/C1SC00221J.
doi: 10.1039/C1SC00221J.

Quasi-Biomimetic Ring Contraction Catalyzed by a Cysteine-Based Nucleophile: Total Synthesis of Sch-642305, Some Analogs and their Putative anti-HIV Activities

Alpay Dermenci  1 , Philipp S Selig, Robert A Domaoal, Krasimir A Spasov, Karen S Anderson, Scott J Miller
Affiliations

Quasi-Biomimetic Ring Contraction Catalyzed by a Cysteine-Based Nucleophile: Total Synthesis of Sch-642305, Some Analogs and their Putative anti-HIV Activities

Alpay Dermenci et al. Chem Sci. .

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-catalyzed 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.

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Figures

Figure 1
Figure 1
A plausible biosynthetic route to Sch-642305.
Figure 2
Figure 2
Retrosynthetic analysis that allows for possible condition-dependent synthesis of stereoisomeric analogs.
Figure 3
Figure 3
Cysteine-catalyzed Rauhut-Currier ring contraction.
Figure 4
Figure 4
Testing of compounds toward HIV-1 in MT-2 human T-cells.
Scheme 1
Scheme 1
Scheme 2
Scheme 2
Scheme 3
Scheme 3
Scheme 4
Scheme 4
Scheme 5
Scheme 5
See this image and copyright information in PMC

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