An olefin metathesis approach towards the solomonamides.

Abstract

A new synthetic strategy directed towards the solomonamides, a novel class of cyclopeptides of marine origin, has been developed utilizing an olefin metathesis reaction to form the [15]-membered ring contained in these natural products. We demonstrated the efficiency and validity of this synthetic approach for the construction of the macrocyclic core of the solomonamides in a minimally oxidized system. In fact, the olefin metathesis cyclization proceeded in a stereoselective manner to provide exclusively the Z-isomer in high yield. The described synthetic strategy for the solomonamides allows for access to the natural products, as well as offering the opportunity for the generation of a diverse set of analogues in the subsequent oxidation phase