Total synthesis of nafuredin, a selective NADH-fumarate reductase inhibitor.
[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.
Takano
D
D
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.
Nagamitsu
T
T
Ui
H
H
Shiomi
K
K
Yamaguchi
Y
Y
Masuma
R
R
Kuwajima
I
I
Omura
S
S
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
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