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Paper | Special issue | Vol 82, No. 1, 2010, pp.491-504
Published online, 2nd June, 2010
DOI: 10.3987/COM-10-S(E)22
Asymmetric Syntheses of Highly Functionalized Bicyclo[2.2.2]octene Derivatives

Masafumi Iwatsu, Daisuke Urabe, and Masayuki Inoue*

*Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan

Abstract

Highly functionalized bicyclo[2.2.2]octene derivatives bearing two quaternary carbon centers were synthesized in an asymmetric fashion. The key transformations were the regioselective Diels-Alder reaction between 3,6-dimethyl-o-quinone monoacetal and 1,1-diethoxyethylene and the subsequent enzymatic resolution. The optically active bicyclo[2.2.2]octene derivatives obtained should serve as versatile chiral building blocks for highly functionalized natural products such as ryanodine.