title: Total synthesis and structural revision of the piperarborenines via sequential cyclobutane C-H arylation.
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.
authors: Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
authors: Will R
authors: WR
authors: Gutekunst
authors: Phil S
authors: PS
authors: Baran
mesh_terms: D003503:Cyclobutanes / Q000737:chemistry*; D015394:Molecular Structure; D010881:Piperidones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D003503:Cyclobutanes; D010881:Piperidones; C570724:piperarborenine B; C570723:piperarborenine D