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Paper | Special issue | Vol 52, No. 3, 2000, pp.1191-1201
Published online, 1st January, 1970
DOI: 10.3987/COM-99-S117
An Asymmetrical Total Synthesis of a Potent Immunosuppressant, Mycestericins D and F, through an Aldol Reaction Using L-Threonine Aldolase

Kiyoharu Nishide, Kayoko Shibata, Tetsuro Fujita, Tetsuya Kajimoto, Chi-Huey Wong, and Manabu Node*

*Kyoto Pharmaceutical University, Misasagi, Yamashina, Kyoto 607-8414, Japan


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.