Total synthesis and biological evaluation of (-)-atrop-abyssomicin C
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.
Source:
Organic & Biomolecular Chemistry, 2013, 11, 33, 5413-5424Publisher:
- Royal Soc Chemistry, Cambridge
Projects:
- The development of new synthetic methods and their application in the synthesis of natural products and biologically active molecules (RS-172027)
- Reinforcement of the Faculty of Chemistry, University of Belgrade, towards becoming a Center of Excellence in the region of WB for Molecular Biotechnology and Food research (EU-256716)
DOI: 10.1039/c3ob40692j
ISSN: 1477-0520
PubMed: 23839049