Formal total synthesis of (−)-balanol: a potent PKC inhibitor

An efficient formal total synthesis of the PKC inhibitor balanol 1 is described, starting from the commercially available pentane1,5-diol. A Shi epoxidation and Pd(0)-mediated nitrogen substitution with double inversion established the correct configuration of the balanol precursor 3.

An efficient formal total synthesis of the PKC inhibitor balanol 1 is described, starting from the commercially available pentane1,5-diol. A Shi epoxidation and a Pd(0)-mediated nitrogen substitution with double inversion are the key steps to establish the correct configuration of the balanol precursor 3.