Stereocontrolled Synthesis of Kalihinol C

We report a concise chemical synthesis
of kalihinol C via a possible
biosynthetic intermediate, “protokalihinol”, which was
targeted as a scaffold en route to antiplasmodial analogs. High stereocontrol
of the kalihinol framework relies on a heterodendralene cascade to
establish the target stereotetrad. Common problems of regio- and chemoselectivity
encountered in the kalihinol class are explained and solved.