title: Total synthesis and biological evaluation of verticipyrone and analogues.
abstract: [reaction: see text] Total synthesis of verticipyrone, a novel NADH-fumarate reductase inhibitor, has been accomplished by a convergent approach using novel "Reverse Julia olefination" method. During total synthetic studies, we also prepared and evaluated several synthetic verticipyrone analogues, some of which exhibited more potent antiparasitic activity than the natural verticipyrone.
authors.affiliation: School of Infection Control Sciences and Kitasato Institute for Life Sciences, Kitasato University, and The Kitasato Institute, 5-9-1 Shirokane, Minato-ku, Tokyo 108-8641, Japan.
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Shimamura
authors.forename: Toshiaki
authors.initials: T
authors.lastname: Sunazuka
authors.forename: Takashi
authors.initials: T
authors.lastname: Izuhara
authors.forename: Tomoyasu
authors.initials: T
authors.lastname: Hirose
authors.forename: Kazuro
authors.initials: K
authors.lastname: Shiomi
authors.forename: Satoshi
authors.initials: S
authors.lastname: Omura
mesh_terms: D000447:Aldehydes / Q000138:chemical synthesis / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry*; D015394:Molecular Structure; D044925:Oxidoreductases Acting on CH-CH Group Donors / Q000037:antagonists & inhibitors / Q000378:metabolism; D011753:Pyrones / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D000447:Aldehydes; D000475:Alkenes; D011753:Pyrones; C517116:verticipyrone; D044925:Oxidoreductases Acting on CH-CH Group Donors; C020155:fumarate reductase (NADH)