Preparation of chiral 4-benzyloxymethyldihydrofuran-2-one using lipase-catalyzed kinetic resolution: synthesis of (-)-virginiae butanolide C (VB C) |
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| Authors: | Takabe Kunihiko Mase Nobuyuki Matsumura Hidetoshi Hasegawa Takehiro Iida Yasuhiro Kuribayashi Hisashi Adachi Kenji Yoda Hidemi Ao Masato |
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| Institution: | Department of Molecular Science, Faculty of Engineering, Shizuoka University, Hamamatsu, Japan. tcktaka@ipc.shizuoka.ac.jp |
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| Abstract: | 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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