Facile Synthesis of Hydroxy Wilfordic Acid, A Esterifying Unit of Anti-HIV Sesquiterpene Pyridine Alkaloids

作者：Eun Jae Soon; Seo Seung Yong^*

来源：Archives of Pharmacal Research, 2009, 32(12): 1673-1679.

DOI：10.1007/s12272-009-2202-1

• Sesquiterpene pyridine alkaloids
• Tripterygium (Celastraceae)
• Anti-HIV activity
• Hydroxy wilfordic acid
• Asymmetric cyanosilylation
• Stereochemistry determination

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.

• 出版日期2009-12