Title of article :
Stereoselective synthesis of tubuvaline methyl ester and tubuphenylalanine, components of tubulysins, tubulin polymerization inhibitors
Author/Authors :
Shibue، نويسنده , , Taku and Hirai، نويسنده , , Toshihiro and Okamoto، نويسنده , , Iwao and Morita، نويسنده , , Nobuyoshi and Masu، نويسنده , , Hyuma and Azumaya، نويسنده , , Isao and Tamura، نويسنده , , Osamu، نويسنده ,
Abstract :
Synthetic studies of two components of tubulysins, tubulin polymerization inhibitors are described. The highly stereoselective synthesis of tubuvaline methyl ester (2) was accomplished by 1,3-dipolar cycloaddition of nitrone d-6 and acrylic acid derivatives 7 as a key step. The synthesis of tubuphenylalanine (3) was conducted by an aldol reaction of a boron enolate of (S)-4-isopropyl-3-propionyl-2-oxazolidinone (13) with aldehyde 14, readily prepared from phenylalanine, followed by Barton deoxygenation under radical conditions.
