Asymmetric total synthesis of MK8383: the iron-mediated coupling reaction is the only effective method for the construction of the (Z)-trisubstituted side-chain alkene

The first asymmetric total synthesis of MK8383 through the iron-mediated coupling reaction is described. In this total synthesis, the key step was clearly the stereoselective construction of the (Z)-trisubstituted side-chain alkene. Although this problem was seemingly easy to resolve, in fact it presented us an opportunity to evaluate the coupling reactions reported to date, and the iron-mediated coupling reaction was found to be the only effective method for the stereoselective construction of the (Z)-trisubstituted side-chain alkene.

Graphical abstractDownload full-size image