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Pure Appl. Chem. Vol. 74, No. 8, pp. 1359-1368 (2002)

Pure and Applied Chemistry

Vol. 74, Issue 8

Development of a practical synthesis of sumanirole*

Peter G. M. Wuts1,**, Rui Lin Gu1, Jill M. Northuis1, Tricia A. Kwan1, Doris M. Beck2, and Michael J. White2

1Chemical Process Research and Development and 2Bioprocess and Formulation Technology, Pharmacia, Kalamazoo, MI 49001, USA

Abstract: A new synthesis of sumanirole that is being developed to treat Parkinson's disease is described. The basic skeleton is constructed from 8-hydroxyquinoline and elaborated to the key tricylic intermediate 14. Further elaboration affords a 1,2-amino alcohol, which is converted to an aziridine by a new process. Finally, dissolving metal reduction to open the aziridine and protecting group removal affords sumanirole.

** Corresponding author.

* Plenary lecture presented at the 3rd Florida Conference on Heterocyclic Chemistry (FloHet-III), Gainesville, Florida, USA, 6-8 March 2002. Other lectures are published in this issue, pp. 1317–1368.

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