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Enantioselective total syntheses of novel PKC activator (+)-decursin and its derivatives using catalytic asymmetric epoxidation of an enone

โœ Scribed by Tetsuhiro Nemoto; Takashi Ohshima; Masakatsu Shibasaki

Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
99 KB
Volume
41
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

The catalytic asymmetric total syntheses of (+)-decursin and three related natural products, (+)-decursinol, (-)-prantschimgin and (+)-marmesin, were achieved for the first time using catalytic asymmetric epoxidation of an enone as the key step. The catalytic asymmetric epoxidation of enone was found to be promoted effectively by novel multifunctional asymmetric catalyst generated from La(O-i-Pr) 3 , BINOL and O AsPh 3 in a 1:1:1 ratio to afford epoxide in 94% yield and 96% ee, which was recrystallized to give the optically pure epoxide.

๐Ÿ“œ SIMILAR VOLUMES

Enantioselective total syntheses of (+)-
Enantioselective total syntheses of (+)-decursin and related natural compounds using catalytic asymmetric epoxidation of an enone
โœ Tetsuhiro Nemoto; Takashi Ohshima; Masakatsu Shibasaki ๐Ÿ“‚ Article ๐Ÿ“… 2003 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 326 KB

The enantioselective total syntheses of (รพ)-decursin (1) and related natural dihydropyranocoumarins (2)-prantschimgin (3), (รพ)decursinol (4), and (รพ)-marmesin (5) were achieved for the first time using catalytic asymmetric epoxidation of an enone as the key step. Catalytic asymmetric epoxidation of