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.