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Issue 41, 2014
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Enantioselective total syntheses of the proposed structures of prevezol B and evaluation of anti-cancer activity

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Abstract

The first enantioselective total syntheses of the proposed structures of the natural product prevezol B are reported. The reported syntheses complement the previously-reported syntheses of the proposed structures of prevezol C, a stereoisomer of prevezol B. It was previously shown that the structure of the naturally occurring prevezol C had been incorrectly assigned. This work has led us to conclude that the proposed structures of prevezol B are also incorrect and major revision of both of the structures of the prevezols B and C is required. Cytotoxicity studies on the human cervical cancer cell line HeLa revealed that the synthesized prevezol B and C compounds were not active even at the highest concentration used (100 μM). However, one of the synthetic precursors was shown to have modest potency against HeLa cells (IC50 = 23.5 ± 1.8 μM).

Graphical abstract: Enantioselective total syntheses of the proposed structures of prevezol B and evaluation of anti-cancer activity

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Supplementary files

Article information


Submitted
05 Aug 2014
Accepted
28 Aug 2014
First published
01 Sep 2014

Org. Biomol. Chem., 2014,12, 8239-8246
Article type
Paper
Author version available

Enantioselective total syntheses of the proposed structures of prevezol B and evaluation of anti-cancer activity

A. E. Leung, R. Rubbiani, G. Gasser and K. L. Tuck, Org. Biomol. Chem., 2014, 12, 8239
DOI: 10.1039/C4OB01662A

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