Takabe Kunihiko, Mase Nobuyuki, Matsumura Hidetoshi, Hasegawa Takehiro, Iida Yasuhiro, Kuribayashi Hisashi, Adachi Kenji, Yoda Hidemi, Ao Masato
Department of Molecular Science, Faculty of Engineering, Shizuoka University, Hamamatsu, Japan.
Bioorg Med Chem Lett. 2002 Sep 2;12(17):2295-7. doi: 10.1016/s0960-894x(02)00458-4.
Lipase-catalyzed kinetic resolution of the N,N-dialkyl-3-benzyloxymethyl-4-hydroxybutanamide 10a,b afforded the acetate 11a,b with (R) configuration, whereas the N-monoalkyl-3-benzyloxymethyl-4-hydroxybutanamide 10c-e gave the acetate 11c-e with (S) configuration. The butanamide 10 smoothly cyclized to give chiral 4-benzyloxymethyldihydrofuran-2-one 9 without racemization, which was effectively transformed into highly stereocontrolled virginiae butanolide C (VB C).
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