title: Enantioselective synthesis of 8-epi-xanthatin and biological evaluation of xanthanolides and their derivatives.
abstract: An enantioselective synthesis of 8-epi-xanthatin (9) has been accomplished starting from the bicyclic lactone 3, which has been used for the synthesis of other xanthanolides, sundiversifolide (4) and diversifolide (5), through a synthetic route without the use of a selenium species. Additionally we have evaluated antimicrobial activities of five natural xanthanolides and their derivatives. Although the synthetic xanthanolides did not show any activity against methicillin-resistant Staphylococcus aureus (MRSA), some of the synthetic intermediates did exhibit moderate antimicrobial activities.
authors.affiliation: Graduate School of Pharmaceutical Sciences, The University of Tokushima, 1-78-1 Sho-machi, Tokushima 770-8505, Japan.
authors.forename: Hiromasa
authors.initials: H
authors.lastname: Yokoe
authors.forename: Kentaro
authors.initials: K
authors.lastname: Noboru
authors.forename: Yuki
authors.initials: Y
authors.lastname: Manabe
authors.forename: Masahiro
authors.initials: M
authors.lastname: Yoshida
authors.forename: Hirofumi
authors.initials: H
authors.lastname: Shibata
authors.forename: Kozo
authors.initials: K
authors.lastname: Shishido
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D005658:Fungi / Q000187:drug effects; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D006801:Humans; D055624:Methicillin-Resistant Staphylococcus aureus / Q000187:drug effects; D009181:Mycoses / Q000188:drug therapy; D011552:Pseudomonas Infections / Q000188:drug therapy; D011550:Pseudomonas aeruginosa / Q000187:drug effects; D013203:Staphylococcal Infections / Q000188:drug therapy; D013237:Stereoisomerism
chemical_list: D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D005663:Furans; C022186:xanthatin