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. 2006 May 11;8(10):2111-3.
doi: 10.1021/ol060503v.

A new approach to the furan degradation problem involving ozonolysis of the trans-enedione and its use in a cost-effective synthesis of eplerenone

Bruce A Pearlman  1 , Amphlett G Padilla, John T Hach, Jeffrey L Havens, Muniraj D Pillai
Affiliations

A new approach to the furan degradation problem involving ozonolysis of the trans-enedione and its use in a cost-effective synthesis of eplerenone

Bruce A Pearlman et al. Org Lett. .

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.

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