Towards the total synthesis of (−)-Curcumene and (−)-Curcuquinone

Abstract

The synthesis of chiral natural products has long been the focal point in the field of asymmetric catalysis since both stereoisomers usually have different bioactivity. Within all the catalytic asymmetric methodologies, homogeneous transition-metal catalyzed hydrogenation plays a pivotal role. Our group has been working in the Ir-catalyzed asymmetric hydrogenation reactions of several substrates such as sulfones, which are versatile building blocks in synthetic chemistry. In this respect, the group recently developed a methodology to synthesize homoallylic sulfones through a highly selective process which has set the stage for the synthesis of different natural products. The previously mentioned methodologies have established the framework for the synthesis and the Ir-catalyzed asymmetric hydrogenation of homoallylic sulfones. In the present work, the applicability of these methodologies has been demonstrated through the synthesis of (+)-⍺-curcumene 1 and an advanced intermediate of (−)-curcuquinone 2.