Enantioselective Synthesis of Bicyclo[2.2.2]octenones Using a Copper-Mediated Oxidative Dearomatization/[4 + 2] Dimerization Cascade1

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J. Am. Chem. Soc., 130 (9), 2738 -2739, 2008. 10.1021/ja711018z S0002-7863(71)01018-7
Web Release Date: February 12, 2008

Enantioselective Synthesis of Bicyclo[2.2.2]octenones Using a Copper-Mediated Oxidative Dearomatization/[4 + 2] Dimerization Cascade¹

Suwei Dong, Jianglong Zhu, and John A. Porco, Jr.*

Department of Chemistry and Center for Chemical Methodology and Library Development (CMLD-BU), Boston University, Boston, Massachusetts 02215

porco@bu.edu

Received December 11, 2007

Abstract:

An enantioselective approach to bicyclo[2.2.2]octenone structures utilizing a copper-mediated asymmetric oxidative dearomatization/[4 + 2] dimerization cascade is described. The total synthesis and absolute stereochemistry reassignment of (+)-aquaticol has been achieved using the methodology.

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