170. Application of the combined C–H activation/Cope rearrangement as a key step in the total syntheses of the assigned structure of (+)-elisabethadione and a (+)-p-benzoquinone natural product

Authors: Huw M.L. Davies, Xing Dai

Tetrahedron,

200662, 45, 10477-10484

 009

The enantioselective total syntheses of the assigned structure of (+)-elisabethadione (3) and the (+)-p-benzoquinone natural product 4 is described. The stereocontrolled formation of the three key stereocenters in the natural products is achieved in a single step through the combined C–H activation/Cope rearrangement, a C–H functionalization process catalyzed by the dirhodium tetraprolinate, Rh2(R-DOSP)4 (DOSP=(N-dodecylbenzenesulfonyl)prolinate).

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