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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.

SUBMITTER: Gutekunst WR

PROVIDER: S-EPMC3223735 | biostudies-literature | 2011 Nov

REPOSITORIES: biostudies-literature

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Total synthesis and structural revision of the piperarborenines via sequential cyclobutane C-H arylation.

Gutekunst Will R WR Baran Phil S PS

Journal of the American Chemical Society 20111108 47

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 cyclobutan ...[more]

PMID: 22066860

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