Asymmetric total synthesis of pseurotin A.
The asymmetric total syntheses of pseurotin A and 8-O-demethylpseurotin A have been accomplished. Key reactions are a NaH-promoted intramolecular cyclization of an alkynylamide to form a gamma-lactam, an aldol reaction of a benzylidene-substituted ketone, and the late-stage introduction of the benzoyl group by a selective oxidation of a benzylidene moiety with dimethyldioxirane (DMD). [reaction: see text]
Hayashi
Yujiro
Y
Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan. hayashi@ci.kagu.tus.ac.jp
Shoji
Mitsuru
M
Yamaguchi
Shinpei
S
Mukaiyama
Takasuke
T
Yamaguchi
Junichiro
J
Kakeya
Hideaki
H
Osada
Hiroyuki
H
D001597:Benzylidene Compounds / Q000737:chemistry; D003500:Cyclization; D007769:Lactams / Q000737:chemistry; D010084:Oxidation-Reduction; D011760:Pyrrolidinones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D001597:Benzylidene Compounds; D007769:Lactams; D011760:Pyrrolidinones; C012013:pseurotin