Facile synthesis of hydroxy wilfordic acid, a esterifying unit of anti-HIV sesquiterpene pyridine alkaloids.
Sesquiterpene pyridine alkaloids were isolated mainly from plants of the genus Tripterygium (Celastraceae) which have been used traditionally in Chinese medicine. These compounds have polyhydroxy dihydro-beta-agarofuran core and esterifying substituent with dilactone bridges, and recently demonstrated promising anti-HIV activity. We have achieved the synthesis of hydroxy wilfordic acid and its ester via asymmetric cyanosilylation. With a NMR study of (S)- and (R)-PGME (phenylglycine methyl ester) amide, the tertiary alcohol stereochemistry of synthetic hydroxyl wilfordic acids was determined. Our synthetic approach will provide a contribution to the synthesis of sesquiterpene pyridine alkaloids and the development of their analogs for anti-HIV activity.
Eun
Jae Soon
JS
College of Pharmacy, Woosuk University, Wanju Jeonbuk, 565-701, Korea.
Seo
Seung-Yong
SY
D000470:Alkaloids / Q000737:chemistry*; D019380:Anti-HIV Agents / Q000138:chemical synthesis*; D002384:Catalysis; D006885:Hydroxybutyrates / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D009525:Niacin / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D011725:Pyridines / Q000737:chemistry*; D012717:Sesquiterpenes / Q000737:chemistry*; D029757:Tripterygium / Q000737:chemistry
D000470:Alkaloids; D019380:Anti-HIV Agents; D006885:Hydroxybutyrates; D007202:Indicators and Reagents; D011725:Pyridines; D012717:Sesquiterpenes; C549415:hydroxy wilfordic acid; D009525:Niacin