Total synthesis and structural revision of the piperarborenines via sequential cyclobutane C-H arylation |
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Authors: | Gutekunst Will R Baran Phil S |
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Institution: | Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA. |
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Abstract: | A strategy for the construction of unsymmetrical cyclobutanes using C-H functionalization logic is demonstrated in the total synthesis of piperarborenine B and piperarborenine D (reported structure). These syntheses feature a new preparation of cis-cyclobutane dicarboxylates from commercially available coumalate starting materials and a divergent approach to the controlled cis or trans installation of the two distinct aryl rings found in the natural products using the first example of cyclobutane C-H arylation. The structure of piperarborenine D is reassigned to a head-to-head dimer, which was synthesized using an intramolecular 2+2] photocycloaddition strategy. |
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