471295-99-5Relevant articles and documents
Process development and scale-up of the potential thiazolidinedione antidiabetic candidate PNU-91325
Carpenter, Donald E.,Imbordino, Rick J.,Maloney, Mark T.,Moeslein, Jeffery A.,Reeder, Michael R.,Scott, Allen
, p. 721 - 728 (2002)
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.