title: Total synthesis of nafuredin, a selective NADH-fumarate reductase inhibitor.
abstract: [structure: see text] Total synthesis of nafuredin, a selective NADH-fumarate reductase inhibitor, has been accomplished by a convergent approach. The C1-C8 and C9-C18 segments were derived efficiently from D-glucose and (S)-(-)-2-methyl-1-butanol, respectively, coupled by stereoselective Julia olefination, and converted to nafuredin.
authors.affiliation: School of Pharmaceutical Science, Kitasato University, Kitasato Institute for Life Sciences, Kitasato University, and CREST, The Japan Science and Technology Corporation (JST), 5-9-1 Shirokane, Minato-ku, Tokyo 108-8641, Japan.
authors.forename: D
authors.initials: D
authors.lastname: Takano
authors.forename: T
authors.initials: T
authors.lastname: Nagamitsu
authors.forename: H
authors.initials: H
authors.lastname: Ui
authors.forename: K
authors.initials: K
authors.lastname: Shiomi
authors.forename: Y
authors.initials: Y
authors.lastname: Yamaguchi
authors.forename: R
authors.initials: R
authors.lastname: Masuma
authors.forename: I
authors.initials: I
authors.lastname: Kuwajima
authors.forename: S
authors.initials: S
authors.lastname: Omura
mesh_terms: D000871:Anthelmintics / Q000138:chemical synthesis*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis*; D005947:Glucose / Q000737:chemistry; D010088:Oxidoreductases / Q000037:antagonists & inhibitors*; D044925:Oxidoreductases Acting on CH-CH Group Donors; D000439:Pentanols / Q000737:chemistry; D011753:Pyrones / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D000871:Anthelmintics; D004791:Enzyme Inhibitors; D000439:Pentanols; D011753:Pyrones; C423563:nafuredin; D010088:Oxidoreductases; D044925:Oxidoreductases Acting on CH-CH Group Donors; C020155:fumarate reductase (NADH); D005947:Glucose