title: Preparation of chiral 4-benzyloxymethyldihydrofuran-2-one using lipase-catalyzed kinetic resolution: synthesis of (-)-virginiae butanolide C (VB C).
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).
authors.affiliation: Department of Molecular Science, Faculty of Engineering, Shizuoka University, Hamamatsu, Japan. tcktaka@ipc.shizuoka.ac.jp
authors.forename: Kunihiko
authors.initials: K
authors.lastname: Takabe
authors.forename: Nobuyuki
authors.initials: N
authors.lastname: Mase
authors.forename: Hidetoshi
authors.initials: H
authors.lastname: Matsumura
authors.forename: Takehiro
authors.initials: T
authors.lastname: Hasegawa
authors.forename: Yasuhiro
authors.initials: Y
authors.lastname: Iida
authors.forename: Hisashi
authors.initials: H
authors.lastname: Kuribayashi
authors.forename: Kenji
authors.initials: K
authors.lastname: Adachi
authors.forename: Hidemi
authors.initials: H
authors.lastname: Yoda
authors.forename: Masato
authors.initials: M
authors.lastname: Ao
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D000215:Acylation; D002384:Catalysis; D005663:Furans; D007700:Kinetics; D008049:Lipase; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry
chemical_list: C475701:4-benzyloxymethyldihydrofuran-2-one; D005663:Furans; C475702:virginiae butanolide C; D008049:Lipase; D015107:4-Butyrolactone