A new approach to the furan degradation problem involving ozonolysis of the trans-enedione and its use in a cost-effective synthesis of eplerenone |
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Authors: | Pearlman Bruce A Padilla Amphlett G Hach John T Havens Jeffrey L Pillai Muniraj D |
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Institution: | Chemical Research and Development, Pfizer, Incorporated, Kalamazoo, Michigan 49001-0102, USA. bruce.pearlman@spcorp.com |
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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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