A New Approach to the Furan Degradation Problem Involving Ozonolysis of the trans-Enedione and Its Use in a Cost-Effective Synthesis of Eplerenone

A New Approach to the Furan Degradation Problem Involving Ozonolysis of the trans-Enedione and Its Use in a Cost-Effective Synthesis of Eplerenone

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 appr...

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Veröffentlicht in:Organic letters 2006-05, Vol.8 (10), p.2111-2113
Hauptverfasser: Pearlman, Bruce A, Padilla, Amphlett G, Hach, John T, Havens, Jeffrey L, Pillai, Muniraj D
Format: Artikel
Sprache:eng
Schlagworte:
Catalysis
Furans - chemistry
Molecular Structure
Ozone - chemistry
Spironolactone - analogs & derivatives
Spironolactone - chemical synthesis
Spironolactone - economics
Stereoisomerism
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Zusammenfassung: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol060503v