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KMID : 0043320090320121673
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Archives of Pharmacal Research
2009 Volume.32 No. 12 p.1673 ~ p.1679
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Facile Synthesis of Hydroxy Wilfordic Acid, A Esterifying Unit of Anti- HIV Sesquiterpene Pyridine Alkaloids
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Seo Seung-Yong
Eun Jae-Soon
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Abstract
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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-β-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.
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KEYWORD
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Sesquiterpene pyridine alkaloids, Tripterygium (Celastraceae), Anti-HIV activity, Hydroxy wilfordic acid, Asymmetric cyanosilylation, Stereochemistry determination
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