| Autor: |
Haight, A. R., Bailey, A. E., Baker, W. S., Cain, M. H., Copp, R. R., DeMattei, J. A., Ford, K. L., Henry, R. F., Hsu, M. C., Keyes, R. F., King, S. A., McLaughlin, M. A., Melcher, L. M., Nadler, W. R., Oliver, P. A., Parekh, S. I., Patel, H. H., Seif, L. S., Staeger, M. A., Wayne, G. S., Wittenberger, S. J., Zhang, W. |
| Zdroj: |
Organic Process Research & Development; November 2004, Vol. 8 Issue: 6 p897-902, 6p |
| Abstrakt: |
Fiduxosin (1) has been under development at Abbott Laboratories for the treatment of benign prostatic hyperplasia. A convergent strategy required methodologies for preparation of an enantiomerically pure 3,4-cis-disubstituted pyrrolidine and a 2,3,5-trisubstituted thienopyrazine in a regiospecific manner. A [3+2] cycloaddition of an enantiopure azomethine ylide followed by a diastereoselective crystallization was employed to prepare the benzopyranopyrrolidine in high diastereomeric and enantiomeric purity. Conditions for reduction of an O-aryl lactone susceptible to epimerization were developed, and cyclization of the alcohol/phenol to the ether was accomplished in high yield. The thienopyrazine was prepared by condensation of methyl thioglycolate and a regiospecifically prepared 2-bromo-3-cyano-5-phenylpyrazine. Conditions for effective halogen substitutive deamination to prepare regiospecific trisubstituted pyrazines will be described. |
| Databáze: |
Supplemental Index |
| Externí odkaz: |
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