Efficient synthesis of antiviral agent uprifosbuvir enabled by new synthetic methods

• Published in: Chemical science (Cambridge) Vol. 12; no. 26; pp. 931 - 936
• Main Authors: Klapars, Artis, Chung, John Y. L, Limanto, John, Calabria, Ralph, Campeau, Louis-Charles, Campos, Kevin R, Chen, Wenyong, Dalby, Stephen M, Davis, Tyler A, DiRocco, Daniel A, Hyde, Alan M, Kassim, Amude M, Larsen, Mona Utne, Liu, Guiquan, Maligres, Peter E, Moment, Aaron, Peng, Feng, Ruck, Rebecca T, Shevlin, Michael, Simmons, Bryon L, Song, Zhiguo Jake, Tan, Lushi, Wright, Timothy J, Zultanski, Susan L
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 07.07.2021; Royal Society of Chemistry; The Royal Society of Chemistry
• Subjects: Chemistry; Chemistry, Multidisciplinary; Ferric chloride; Hydrochlorination; Nucleotides; Oxidation; Physical Sciences; Science & Technology; Stereoselectivity; Synthesis; DESIGN; FACILE SYNTHESIS; DERIVATIVES; NUCLEOSIDES

An efficient route to the HCV antiviral agent uprifosbuvir was developed in 5 steps from readily available uridine in 50% overall yield. This concise synthesis was achieved by development of several synthetic methods: (1) complexation-driven selective acyl migration/oxidation; (2) BSA-mediated cycli...