Asymmetric Synthesis of Functionalized trans-Cyclopropoxy Building Block for Grazoprevir
2017
Xu, Feng | Zhong, Yong-Li | Li, Hongming | Qi, Ji | Desmond, Richard | Song, Zhiguo J. | Park, Jeonghan | Wang, Tao | Truppo, Matthew | Humphrey, Guy R. | Ruck, Rebecca T.
A practical and asymmetric synthesis of a functionalized trans-cyclopropoxy building block for the preparation of the HCV NS3/4a protease inhibitor grazoprevir is reported. Intramolecular SN2 displacement–ring closure, followed by a Baeyer–Villiger oxidation, yields the desired trans-cyclopropanol with full control of diastereoselectivity. A terminal alkyne is then effectively installed using LiNH(CH₂)₂NEt₂. Starting from (S)-epichlorohydrin, the cyclopropoxy building block is prepared in 51% overall yield with >99.8% optical purity without isolation of any intermediates.
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