title: Use of a palladium(II)-catalyzed oxidative kinetic resolution in synthetic efforts toward bielschowskysin.
abstract: Progress toward the cyclobutane core of bielshowskysin is reported. The core was thought to arise from a cyclopropane intermediate via a furan-mediated cyclopropane fragmentation, followed by a 1,4-Michael addition. The synthesis of the cyclopropane intermediate utilizes a Suzuki coupling reaction, an esterification with 2-diazoacetoacetic acid, and a copper catalyzed cyclopropanation. An alcohol intermediate within the synthetic route was obtained in high enantiopurity via a highly selective palladium(II)-catalyzed oxidative kinetic resolution (OKR).
authors.affiliation: Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 East California Boulevard, MC 101-20, Pasadena, CA 91125, USA.
authors.forename: Michael E
authors.initials: ME
authors.lastname: Meyer
authors.forename: John H
authors.initials: JH
authors.lastname: Phillips
authors.forename: Eric M
authors.initials: EM
authors.lastname: Ferreira
authors.forename: Brian M
authors.initials: BM
authors.lastname: Stoltz
keywords: Bielschowskysin; palladium; synthesis; transesterification
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