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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 ML Davies  Xing Dai
Institution:Department of Chemistry, University at Buffalo, The State University of New York, Buffalo, NY 14260-3000, USA
Abstract: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).
Keywords:Combined C-H activation/Cope rearrangement  Total synthesis  3)" target="_blank">(+)-Elisabethadione (3)  Rhodium carbenoid  C-H insertion
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