Total Synthesis of Nafuredin, a Selective NADH-fumarate Reductase Inhibitor

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...

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Bibliographic Details
Published inOrganic letters Vol. 3; no. 15; pp. 2289 - 2291
Main Authors Takano, Daisuke, Nagamitsu, Tohru, Ui, Hideaki, Shiomi, Kazuro, Yamaguchi, Yuuichi, Masuma, Rokuro, Kuwajima, Isao, Ōmura, Satoshi
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 26.07.2001
Amer Chemical Soc
Subjects
Anthelmintics - chemical synthesis
Chemistry
Chemistry, Organic
Enzyme Inhibitors - chemical synthesis
Glucose - chemistry
Oxidoreductases - antagonists & inhibitors
Oxidoreductases Acting on CH-CH Group Donors
Pentanols - chemistry
Physical Sciences
Pyrones - chemical synthesis
Science & Technology
Stereoisomerism
DERIVATIVES
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Summary: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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol010089t