Work

Total Synthesis and Structural Revision of the Piperarborenines via Sequential Cyclobutane C–H Arylation

Year: 2011

Type: article

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.

Source: Journal of the American Chemical Society

DOI: 10.1021/ja209205x

Authors: Will R. Gutekunst, Phil S. Baran

Institution: Scripps Research Institute

Language: English

Topic: Catalytic C–H Functionalization Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: National Institutes of Health, National Institute of General Medical Sciences

Awards: Synthesis of Pyrrole-Imidazole Alkaloids, G963544812