Total synthesis and biological evaluation of verticipyrone and analogues.
[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.
Shimamura
Hiroyuki
H
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.
Sunazuka
Toshiaki
T
Izuhara
Takashi
T
Hirose
Tomoyasu
T
Shiomi
Kazuro
K
Omura
Satoshi
S
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
D000447:Aldehydes; D000475:Alkenes; D011753:Pyrones; C517116:verticipyrone; D044925:Oxidoreductases Acting on CH-CH Group Donors; C020155:fumarate reductase (NADH)