Process Development and Scale-Up of the Potential Thiazolidinedione Antidiabetic Candidate PNU-91325

An efficient six-step synthesis has been developed for the preparation of the thiazolidinedione analogue PNU-91325 (3) from the commercially available olefin 12. This process involves a novel epoxide ring opening with a deactivated phenol under phase-transfer conditions. Significant improvements wer...

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Bibliographic Details
Published in:Organic process research & development 2002-09, Vol.6 (5), p.721-728
Main Authors: Carpenter, Donald E, Imbordino, Rick J, Maloney, Mark T, Moeslein, Jeffery A, Reeder, Michael R, Scott, Allen
Format: Article
Language:English
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Summary:An efficient six-step synthesis has been developed for the preparation of the thiazolidinedione analogue PNU-91325 (3) from the commercially available olefin 12. This process involves a novel epoxide ring opening with a deactivated phenol under phase-transfer conditions. Significant improvements were made in the oxidation of a secondary alcohol to the ketone and the 1,4-reduction of an enone from a previous process. Overall, this route allows for the preparation of PNU-91325 in 25% yield.
ISSN:1083-6160
1520-586X
DOI:10.1021/op025549s