Organic Process Research and Development p. 721 - 728 (2002)
Update date:2022-08-02
Topics:
Carpenter, Donald E.
Imbordino, Rick J.
Maloney, Mark T.
Moeslein, Jeffery A.
Reeder, Michael R.
Scott, Allen
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.
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Doi:10.1021/np0201570
(2002)Doi:10.1039/b201229d
(2002)Doi:10.1021/ol026746e
(2002)Doi:10.1002/jhet.5570410609
(2004)Doi:10.1016/S0040-4020(02)00723-8
(2002)Doi:10.1021/om020334s
(2002)
