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Asymmetric Synthesis of CDP840 by Jacobsen Epoxidation. An Unusual Syn Selective Reduction of an Epoxide

1997; American Chemical Society; Volume: 62; Issue: 26 Linguagem: Inglês

10.1021/jo971476c

1520-6904

Joseph E. Lynch, Woo‐Baeg Choi, Hywyn Churchill, R. P. Volante, Robert A. Reamer, Richard G. Ball,

Organic Chemistry Cycloaddition Reactions

An asymmetric synthesis of the PDE IV inhibitor, CDP840 (3) is reported. The absolute stereochemistry was controlled by a Jacobsen epoxidation of the Z triaryl olefin 8 (89% ee) or the E triaryl olefin 9 (48% ee). The disparate results in stereocontrol were interpreted in terms of the "skewed side-on approach model" proposed by Jacobsen. LiBH4·BH3 reduction of the epoxides was found to proceed with retention of configuration.