Journal of the American Chemical Society, Vol.139, No.10, 3647-3650, 2017
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.