A scaleable synthesis of fiduxosin

AR Haight, AE Bailey, WS Baker, MH Cain…

Index: Haight, Anthony R.; Bailey, Anne E.; Baker, William S.; Cain, Michael H.; Copp, Richard R.; Demattei, John A.; Ford, Kelley L.; Henry, Rodger F.; Hsu, Margaret C.; Keyes, Robert F.; King, Steven A.; McLaughlin, Maureen A.; Melcher, Laura M.; Nadler, William R.; Oliver, Patricia A.; Parekh, Shyamal I.; Patel, Hemant H.; Seif, Louis S.; Staeger, Mike A.; Wayne, Gregory S.; Wittenberger, Steven J.; Zhang, Weijiang Organic Process Research and Development, 2004 , vol. 8, # 6 p. 897 - 902

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Citation Number: 39

Abstract

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 ...

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