| Abstract: | ![]()
The synthesis of quinic acid ( 4 ) via epoxide 13 , starting from shikimic acid ( 5 ), is described (Scheme 1). Treatment of 13 with thiophenol yielded not only 17 , but also the γ-lactones 18 and 19 as result of migration of silyl groups within a cis- and trans-diol system. The conversion provides a direct stereoselective epoxidation of a shikimic-acid derivative as well as an alternative pathway for the preparation of 4 . A shorter approach via the disilylated epoxide 22 was unsuccessful because the γ-lactone 25 was obtained in place of the desired α-hydroxy ester 24 (Scheme 2). |
