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