title: A new approach to the furan degradation problem involving ozonolysis of the trans-enedione and its use in a cost-effective synthesis of eplerenone.
abstract: [reaction: see text] Whereas ozonization of furan 3a affords little or no carboxylic acid 5, ozonization of the corresponding trans-enedione 6 afforded carboxylic acid 5 in 82.4% yield (cryst., overall from furan, 100 g scale; after workup with dimethyl sulfide, followed by mildly basic hydrogen peroxide). This new approach to furan degradation is showcased in a cost-effective synthesis of eplerenone, an important new medicine for cardiovascular indications.
authors: Chemical Research and Development, Pfizer, Incorporated, Kalamazoo, Michigan 49001-0102, USA. bruce.pearlman@spcorp.com
authors: Bruce A
authors: BA
authors: Pearlman
authors: Amphlett G
authors: AG
authors: Padilla
authors: John T
authors: JT
authors: Hach
authors: Jeffrey L
authors: JL
authors: Havens
authors: Muniraj D
authors: MD
authors: Pillai