An alternative synthetic strategy for (3R, 5R)-sonnerlactone and (3R, 5S)-sonnerlactone

A novel stereoselective strategy for the synthesis of both the (3R,5R)-sonnerlactone (1) and (3R,5S)-sonnerlac- tone (1a) was developed, which was accomplished from commercially available 2,4 dimethoxy benzoic acid and known chiral bisepoxides using allylation directed by ortho lithiation, Corey-Seebach reaction, Yamaguchi macrolactonisation and Mitsunobu reaction as key steps.