title: 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.
authors.affiliation: Faculty of Chemistry, University of Belgrade, Studentski trg 16, POB 51, 11158 Belgrade 118, Serbia.
authors.forename: Filip
authors.initials: F
authors.lastname: Bihelovic
authors.forename: Ivanka
authors.initials: I
authors.lastname: Karadzic
authors.forename: Radomir
authors.initials: R
authors.lastname: Matovic
authors.forename: Radomir N
authors.initials: RN
authors.lastname: Saicic
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects*; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology* / Q000633:toxicity; D002384:Catalysis; D002470:Cell Survival / Q000187:drug effects; D006046:Gold / Q000737:chemistry; D006367:HeLa Cells; D006801:Humans; D007963:Leukocytes, Mononuclear / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000900:Anti-Bacterial Agents; D019086:Bridged Bicyclo Compounds, Heterocyclic; C509797:abyssomicin C; D006046:Gold