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Published September 9, 2013 | Accepted Version
Journal Article Open

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


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).

Additional Information

© 2013 Elsevier Ltd. Received 18 December 2012; Received in revised form 8 February 2013; Accepted 8 February 2013; Available online 19 February 2013. The authors are grateful to the NIH-NIGMS (R01GM080269), the Bristol-Myers Squibb Company (predoctoral fellowship to E.M.F.), California Institute of Technology, A. P. Sloan Foundation, the Dreyfus Foundation, Research Corporation, Abbott (d), Amgen, AstraZeneca, Boehringer-Ingelheim, GlaxoSmithKline, Johnson and Johnson, Eli Lilly, Merck, Novartis, Pfizer, and Roche for generous funding.

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Accepted Version - nihms447820.pdf


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