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Asymmetric Synthesis of Triazole Antifungal Agents Enabled by an Upgraded Strategy for the Key Epoxide Intermediate.

Yu TangZhuo LiMeiqi ZengRan LiHao SongDan ZhangFei XueYong Qin
Published in: The Journal of organic chemistry (2024)
A streamlined and efficient approach to the key epoxide intermediate for the asymmetric synthesis of triazole antifungal agents is presented. This synthesis highlights a P(NMe 2 ) 3 -mediated nonylidic olefination of α-keto ester, ensuring the exclusive formation of the requisite ( Z )-alkene, followed by a highly enantioselective Jacobsen epoxidation to establish the two vicinal stereocenters in a single step. The versatility of this strategy is exemplified through the efficient synthesis of efinaconazole and ravuconazole.
Keyphrases
  • candida albicans