An asymmetric total synthesis of a potent immunosuppressant, mycestericins D and F, through an aldol reaction using L-threonine aldolase

Article abstract of DOI:10.3987/com-99-s117

L-Threonine aldolase from Candida humicola catalyzed the aldol reaction of 4-benzyloxybutanal (1) with glycine to give β-hydroxy-α-amino acids (2e,t), whose erythro / threo ratio was controlled by using either kinetic or thermodynamic conditions. The erythro derivative (4e) was effectively converted to mycestericins D and F via a stereoselective hydroxymethylation of oxazoline derivative (6) as the key step.