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ChemInform Abstract: Asymmetric Synthesis of CDP840 by Jacobsen Epoxidation. An Unusual Syn-Selective Reduction of an Epoxide.

✍ Scribed by J. E. LYNCH; W.-B. CHOI; H. R. O. CHURCHILL; R. P. VOLANTE; R. A. REAMER; R. G. BALL

Publisher: John Wiley and Sons
Year: 2010
Weight: 37 KB
Volume: 29
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199818159

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✦ Synopsis

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

-The catalytic asymmetric synthesis of the PDE (IV) inhibitor, CDP840 (R)-(VI), useful as antiasthmatic agent, is presented. The absolute stereochemistry is controlled by a Jacobsen epoxidation of the olefin (I). The chiral epoxide (II) is reduced with LiBH 4 /BH 3 with retention of the configuration. Similarly obtained is the enantiomeric (VI) from (III) via the chiral epoxide (IV). -(LYNCH,

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