A New Approach to the Furan Degradation Problem Involving Ozonolysis of the trans-Enedione and Its Use in a Cost-Effective Synthesis of Eplerenone
| Autor: | Bruce Allen Pearlman, Hach Jt, Pillai, Havens Jeffrey L, Amphlett Greg Padilla |
|---|---|
| Rok vydání: | 2006 |
| Předmět: |
chemistry.chemical_classification
Ozonolysis Molecular Structure Degradation Problem Carboxylic acid Organic Chemistry Stereoisomerism Spironolactone Biochemistry Catalysis Eplerenone chemistry.chemical_compound Ozone chemistry Furan Yield (chemistry) medicine Organic chemistry Dimethyl sulfide Physical and Theoretical Chemistry Furans Hydrogen peroxide medicine.drug |
| Zdroj: | Organic Letters. 8:2111-2113 |
| ISSN: | 1523-7052 1523-7060 |
| Popis: | [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. |
| Databáze: | OpenAIRE |
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