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Issue 33, 2013
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Total synthesis and biological evaluation of (−)-atrop–abyssomicin C

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Abstract

Enantioselective synthesis of a marine antibiotic (−)-atrop–abyssomicin C was accomplished in 21 steps, in 1.8% overall yield (4%, based on the recovered starting material). The key steps of the synthesis are the formation of the functionalized cyclohexane core by an organocatalyzed Tsuji–Trost reaction, the formation of a tricyclic spirotetronate unit by a gold-catalyzed reaction sequence and the highly efficient eleven-membered ring closure by a Nozaki–Hiyama–Kishi reaction. Biological tests showed all abyssomicin derivatives to possess strong antibacterial activity against methicillin resistant S. aureus strains; however, they also proved to be cytotoxic, both to malignant and to normal somatic cells.

Graphical abstract: Total synthesis and biological evaluation of (−)-atrop–abyssomicin C

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Supplementary files

Article information


Submitted
06 Apr 2013
Accepted
18 Jun 2013
First published
19 Jun 2013

Org. Biomol. Chem., 2013,11, 5413-5424
Article type
Paper

Total synthesis and biological evaluation of (−)-atrop–abyssomicin C

F. Bihelovic, I. Karadzic, R. Matovic and R. N. Saicic, Org. Biomol. Chem., 2013, 11, 5413 DOI: 10.1039/C3OB40692J

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