The Stereoselective Construction of All-Carbon Quaternary Stereocenters by Allylations and Its Application to Synthetic Studies of Natural Products

Abstract

The synthesis of organic compounds containing all carbon quaternary stereocenters through the addition of allylmetals to aldehydes is still a challenge. In this account we describe two methods to achieve this transformation stereoselectively: one involves the zinc mediated Barbier type allylation and the other allylboration of a sugar derived aldehyde. These methods were applied to the total synthesis of () vibsanin A, and the synthesis of the tricyclic core of () callophycoic acid A.