A study toward a total synthesis of fostriecin

In order to synthesize the major C(3)C(12) part of fostriecin, asymmetric dihydroxylation of several dienes 5a–f, prepared by cross-coupling reactions of several types, was studied, thus providing high dependency on the hydroxyl groups at C(5) and C(11). The best regioselectivity was obtained with 5d to produce diol 23, which was later transformed into the advanced intermediate 26.