Tetrahedron

Stereoselective total synthesis of (+)-lactacystin from D-glucose

N Chida, J Takeoka, K Ando, N Tsutsumi, S Ogawa

Index: Chida, Noritaka; Takeoka, Jun; Ando, Kohji; Tsutsumi, Noriko; Ogawa, Seiichiro Tetrahedron, 1997 , vol. 53, # 48 p. 16287 - 16298

Full Text: HTML

Citation Number: 72

Abstract

The chiral and stereoselective synthesis of (+)-lactacystin 1, the first non-protein neurotrophic factor having an α, α-disubstituted α-amino acid structure, is described. The highly functionalized γ-lactam portion possessing a tetra-substituted carbon with nitrogen in 1 was effectively constructed from d-glucose using allylic trichloroacetimidate rearrangement (Overman rearrangement) as the key reaction.