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Synfacts 2010(3): 0268-0268
DOI: 10.1055/s-0029-1219299
DOI: 10.1055/s-0029-1219299
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of (S)-L-771688
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
Further Information
Publication History
Publication Date:
18 February 2010 (online)
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.