First asymmetric synthesis of CJ-14877 and its enantiomer and their interleukin-1beta inhibitory activities.
A potent antiinflammatory methyl picolinate alkaloid CJ-14877 [(+)-1] and its enantiomer (-)-1 were synthesized in two steps starting from commercially available methyl 5-bromopicolinate. The synthesis includes microwave-assisted Suzuki coupling reaction and Sharpless asymmetric dihydroxylation.
Aoyagi
Yutaka
Y
Natural Products and Medicinal Chemistry, School of Pharmacy, Tokyo University of Pharmacy & Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan.
Adachi
Yoshiyuki
Y
Akagi
Shunta
S
Ohno
Naohito
N
Takeya
Koichi
K
D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D053583:Interleukin-1beta / Q000037:antagonists & inhibitors* / Q000378:metabolism; D008070:Lipopolysaccharides / Q000378:metabolism; D010848:Picolinic Acids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism
D000893:Anti-Inflammatory Agents; D053583:Interleukin-1beta; D008070:Lipopolysaccharides; D010848:Picolinic Acids; C440625:methyl 5-(7,8-dihydroxypropyl)pyridine-2-carboxylate