Asymmetric Total Synthesis of (-)-Juvabione via Sequential Ir-Catalyzed Hydrogenations.

Abstract

(-)-Juvabione, a natural sesquiterpene exhibiting juvenile insect hormone activity, was synthesized constructing the two adjacent stereogenic centers via sequential Ir-catalyzed hydrogenations. The first center is generated by hydrogenation of a styrene-type double bond (99% ee). The successive monohydrogenation of a diene intermediate constitutes the key step, granting high levels of regio- and stereocontrol (94:6 dr). This novel strategy allowed the preparation of (-)-juvabione from simple starting materials in 9 steps and 17% total yield.