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Novel synthesis of CP-734432, an EP4 agonist, using Sharpless asymmetric dihydroxylation

✍ Scribed by Sajiv K. Nair; Jean J. Matthews; Stephan J. Cripps; Chunrong Ma; Elena Z. Dovalsantos; Alan W. Grubbs; Neal W. Sach; Wolter ten Hoeve; Han Koster; Erik J. Flahive; Steven P. Tanis; Matt Renner; Jim van Wiltenburg

Publisher: Elsevier Science
Year: 2010
Tongue: French
Weight: 456 KB
Volume: 51
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2009.12.092

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✦ Synopsis

A novel and efficient asymmetric route to CP-734432, a lactam analog of PGE2, that shows selective agonism against the EP4 receptor subtype, is reported herein. The key steps include a Heck coupling to introduce the aryl ring at C-16 and a highly diastereoselective Sharpless asymmetric dihydroxylation to set the C-15 center.

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