An enantioselective synthesis of the key intermediate for triazole antifungal agents; Application to the catalytic asymmetric synthesis of efinaconazole (jublia)

Keiji Tamura, Naoya Kumagai, Masakatsu Shibasaki

Research output: Contribution to journalArticlepeer-review

25 Citations (Scopus)

Abstract

A new synthetic route, the shortest reported to date, to access a key intermediate for the synthesis of various triazole antifungal agents was developed. The elusive tetrasubstituted stereogenic center that is essential in advanced triazole antifungal agents was constructed via the catalytic asymmetric cyanosilylation of a ketone. The subsequent transformations were performed in two one-pot operations, enhancing the overall synthetic efficiency toward the intermediate. This streamlined synthetic approach was successfully applied to efficient enantioselective syntheses of efinaconazole (Jublia) and ravuconazole.

Original languageEnglish
Pages (from-to)3272-3278
Number of pages7
JournalJournal of Organic Chemistry
Volume79
Issue number7
DOIs
Publication statusPublished - 2014 Apr 4
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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