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Lipase-catalyzed kinetic resolution of 2,3-epoxy-1-tridecanol and its application to facile synthesis of (+)-disparlure

โœ Scribed by Ei-Ichiro Fukusaki; Shiro Satoda; Shuji Senda; Tetsuo Omata


Book ID
114399782
Publisher
Elsevier Science
Year
1999
Tongue
English
Weight
78 KB
Volume
87
Category
Article
ISSN
1389-1723

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Lipase-catalyzed kinetic resolution of 3
โœ Sadao Tsuboi; Nobuyuki Yamafuji; Masanori Utaka ๐Ÿ“‚ Article ๐Ÿ“… 1997 ๐Ÿ› Elsevier Science ๐ŸŒ English โš– 289 KB

Reduction of 3-chloro-2-oxoalkanoates 1 with NaBH4 gave predominantly syn-3-chloro-2-hydroxyalkanoates 2 (synlanti=9119-9911) in 50--97% yields. Resolution of syn-2 by lipase-catalyzed transesterification gave (2S,3S)-2 and (2R,3R)-2-acetoxy-3chloroalkanoates (2R,3R)-3. Total synthesis of (-)-dispar