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Synfacts 2010(3): 0268-0268  
DOI: 10.1055/s-0029-1219299
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (S)-L-771688

Contributor(s): Philip Kocienski
N. Li, X.-H. Chen, J. Song, S.-W. Luo*, W. Fan, L.-Z. Gong*
University of Science and Technology of China, Heifei, Chengdu Institute of Organic Chemistry and Graduate School of Chinese Academy of Sciences, Beijing, P. R. of China
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Publication History

Publication Date:
18 February 2010 (online)

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Significance

(S)-L-771688 is a selective α1a ­adrenergic receptor antagonist for the treatment of benign prostatic hyperplasia. The key step in the synthesis is the construction of the dihydro­pyrimidinethione E via an organocatalytic asymmetric Biginelli reaction mediated by the enantiopure phosphoric acid diester C. By tuning the size of the substituents on the catalyst C, the ­stereochemistry of the Biginelli reaction can be ­reversed.