A Novel Route for Chiral Synthesis of the Triazole Antifungal ER-30346

Yumiko KAKU; Akihiko TSURUOKA; Hiroyuki KAKINUMA; Itaru TSUKADA; Manabu YANAGISAWA; Toshihiko NAITO

doi:10.1248/cpb.46.1125

Yumiko KAKU, Akihiko TSURUOKA, Hiroyuki KAKINUMA, Itaru TSUKADA, Manabu YANAGISAWA, Toshihiko NAITO

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Keywords: ER-30346, triazole antifungal, diastereoselective synthesis, methyl S-(+)-3-hydroxy-2-methylpropionate

JOURNAL FREE ACCESS

1998 Volume 46 Issue 7 Pages 1125-1129

DOI https://doi.org/10.1248/cpb.46.1125

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Abstract

A novel synthetic route to (2S, 3S)-2-(2, 4-difluorophenyl)-3-hydroxy-2-methyl-4-(1-(1, 2, 4-triazolyl))butyronitrile (2), an intermediate for the orally active triazole antifungal agent ER-30346, was developed from methyl S-(+)-3-hydroxy-2-methylpropionate, a commercially available chiral compound. The second chiral center was constructed with 6.4 : 1 diastereoselectivity via osmium tetroxide catalyzed dihydroxylation.

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