Novel SN2' reactions in terpenoid synthesis

by Ruider, Stefan A.; McIntosh, Matthias C.

In the course of our ongoing synthesis of the antileukemia agent sclerophytin A, we have used an SN2' reaction to form the C1-C2 bond in a diastereoselective manner. Sesquiterpenoid lactone 1 could serve as general intermediate in terpenoid natural product synthesis. We will describe studies of the scope of this novel SN2' reaction using a variety of copper nucleophiles.