Lipase-catalyzed kinetic resolution of 2,3-epoxy-1-tridecanol and its application to facile synthesis of (+)-disparlure.
Acylation of (+/-)-2,3-epoxy-1-tridecanol with acetic anhydride in diisopropyl ether by porcine pancreatic lipase yielded (2R, 3S)-2,3-epoxy-1-tridecanol as the remaining substrate with an optical purity of over 99% ee. (+)-Disparlure was synthesized in two steps from this optically active epoxy alcohol.
Fukusaki
E
E
Department of Biotechnology, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871 Japan.
Satoda
S
S
Senda
S
S
Omata
T
T