Total synthesis and adjuvant activity of all stereoisomers of pinellic acid |
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| Authors: | Shirahata Tatsuya Sunazuka Toshiaki Yoshida Kiminari Yamamoto Daisuke Harigaya Yoshihiko Nagai Takayuki Kiyohara Hiroaki Yamada Haruki Kuwajima Isao Omura Satoshi |
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| Affiliation: | The Kitasato Institute for Life Science, School of Pharmaceutical Science, Kitasato University, Shirokane, Minatoku, Tokyo 108-8641, Japan. |
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| Abstract: | Pinellic acid is a novel and potentially useful oral adjuvant when used in conjunction with intranasal inoculation of influenza HA vaccines. All stereoisomers of pinellic acid have been synthesized via regioselective asymmetric dihydroxylation, regioselective inversion, and stereoselective reduction, and their adjuvant activities were characterized. Among this series of isomers, 9S, 12S, 13S compound has the most potent adjuvant activity. Structure-activity relationships are discussed. |
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