Use of a palladium(II)-catalyzed oxidative kinetic resolution in synthetic efforts toward bielschowskysin

TETRAHEDRON

卷:69

Article

Meyer, Michael E.¹  Phillips, John H.¹  Ferreira, Eric M.¹  Stoltz, Brian M.¹ 

[1] CALTECH, Div Chem & Chem Engn, Pasadena, CA 91125 USA

关键词: Bielschowskysin;    Palladium;    Transesterification;    Synthesis;   

DOI  :  10.1016/j.tet.2013.02.034

来源: Elsevier

【 摘 要 】

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). (C) 2013 Elsevier Ltd. All rights reserved.

【 授权许可】

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