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.
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
** 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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