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Synfacts 2009(10): 1069-1069  
DOI: 10.1055/s-0029-1217862
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (+)-L-733,060

Contributor(s): Philip Kocienski
J. L. Bilke, S. P. Moore, P. O’Brien*, J. Gilday
University of York and AstraZeneca Process R&D, Bristol, UK
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Publication History

Publication Date:
22 September 2009 (online)

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Significance

(+)-L733,060 is a potent and selective neurokinin-1 substance P antagonist, an important lead for the treatment of Alzheimer’s disease. The key step in this asymmetric synthesis is a refinement of the asymmetric deprotonation of N-Boc pyrrolidine (A) by s-BuLi and (-)-sparteine originally reported by Beak and co-workers (J. Am. Chem. Soc. 1994, 116, 3231).