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.