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

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 dihydroxylati...

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Bibliographic Details
Published in:	Tetrahedron letters Vol. 51; no. 11; pp. 1451 - 1454
Main Authors:	Nair, Sajiv K., Matthews, Jean J., Cripps, Stephan J., Ma, Chunrong, Dovalsantos, Elena Z., Grubbs, Alan W., Sach, Neal W., Hoeve, Wolter ten, Koster, Han, Flahive, Erik J., Tanis, Steven P., Renner, Matt, Wiltenburg, Jim van
Format:	Journal Article
Language:	English
Published:	Elsevier Ltd 17-03-2010
Online Access:	Get full text
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Summary:	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. 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.
ISSN:	0040-4039 1873-3581
DOI:	10.1016/j.tetlet.2009.12.092