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Total synthesis of pinellic acid, a potent oral adjuvant for nasal influenza vaccine. Determination of the relative and absolute configuration

✍ Scribed by Toshiaki Sunazuka; Tatsuya Shirahata; Kiminari Yoshida; Daisuke Yamamoto; Yoshihiro Harigaya; Takayuki Nagai; Hiroaki Kiyohara; Haruki Yamada; Isao Kuwajima; Satoshi Ōmura

Book ID: 104232388
Publisher: Elsevier Science
Year: 2002
Tongue: French
Weight: 117 KB
Volume: 43
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)02348-6

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✦ Synopsis

Pinellic acid (1), isolated from a medicinal plant Pinelliae tuber, has potent adjuvant activity. The absolute configuration of pinellic acid was expected by derivatization of this compound and CD exciton chirality method. A convergent synthetic route to pinellic acid has been developed via regioselective asymmetric dihydroxylation and stereoselective reduction. The absolute configuration of pinellic acid was determined to be 9S,12S,13S, by comparing with the spectra data of natural and synthetic compounds.

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