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

摘要

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