Preparation of chiral 4-benzyloxymethyldihydrofuran-2-one using lipase-catalyzed kinetic resolution: synthesis of (-)-virginiae butanolide C (VB C).
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).
Takabe
Kunihiko
K
Department of Molecular Science, Faculty of Engineering, Shizuoka University, Hamamatsu, Japan. tcktaka@ipc.shizuoka.ac.jp
Mase
Nobuyuki
N
Matsumura
Hidetoshi
H
Hasegawa
Takehiro
T
Iida
Yasuhiro
Y
Kuribayashi
Hisashi
H
Adachi
Kenji
K
Yoda
Hidemi
H
Ao
Masato
M
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
C475701:4-benzyloxymethyldihydrofuran-2-one; D005663:Furans; C475702:virginiae butanolide C; D008049:Lipase; D015107:4-Butyrolactone