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Asymmetric Synthesis of Functionalized trans-Cyclopropoxy Building Block for Grazoprevir
- Source :
- Organic Letters; 20240101, Issue: Preprints
- Publication Year :
- 2024
-
Abstract
- 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.
Details
- Language :
- English
- ISSN :
- 15237060 and 15237052
- Issue :
- Preprints
- Database :
- Supplemental Index
- Journal :
- Organic Letters
- Publication Type :
- Periodical
- Accession number :
- ejs43594726
- Full Text :
- https://doi.org/10.1021/acs.orglett.7b02867