Practical Synthesis of a Key Intermediate for Lactacystin from (R)-4-Hydroxymethyl-2-phenyl-4,5-dihydrooxazol-4-ylmethyl Acetate

Hiroaki Miyaoka; Makoto Yamanishi; Ayako Hoshino; Hidemichi Mitome; Etsuko Kawashima

doi:10.1248/cpb.56.738

Notes

Practical Synthesis of a Key Intermediate for Lactacystin from (R)-4-Hydroxymethyl-2-phenyl-4,5-dihydrooxazol-4-ylmethyl Acetate

Hiroaki Miyaoka, Makoto Yamanishi, Ayako Hoshino, Hidemichi Mitome, Etsuko Kawashima

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Keywords: lactacystin, formal synthesis, α-substituted α-amino acid, chiral building block, proteasome inhibitor

JOURNAL FREE ACCESS

2008 Volume 56 Issue 5 Pages 738-741

DOI https://doi.org/10.1248/cpb.56.738

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Abstract

A practical synthesis of a key intermediate for the proteasome inhibitor lactacystin from (R)-4-hydroxymethyl-2-phenyl-4,5-dihydrooxazol-4-ylmethyl acetate was established. (R)-4-Hydroxymethyl-2-phenyl-4,5-dihydrooxazol-4-ylmethyl acetate is a useful chiral building block for the synthesis of biologically active compounds containing α-substituted α-amino acid moieties.

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