Asymmetric total synthesis of (-)-azaspirene, a novel angiogenesis inhibitor.
The asymmetric total synthesis of (-)-azaspirene, an angiogenesis inhibitor, has been accomplished, establishing its absolute stereochemistry. The key steps are a MgBr2.OEt2-mediated, diastereoselective Mukaiyama aldol reaction, a NaH-promoted, intramolecular cyclization of an alkynylamide, and the aldol reaction of a ketone containing functionalized gamma-lactam moiety without protection of tert-alcohol and amide functionalities.
Hayashi
Yujiro
Y
Department of Industrial Chemistry, Faculty of Engineering, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan. hayashi@ci.kagu.tus.ac.jp
Shoji
Mitsuru
M
Yamaguchi
Junichiro
J
Sato
Kenji
K
Yamaguchi
Shinpei
S
Mukaiyama
Takasuke
T
Sakai
Ken
K
Asami
Yukihiro
Y
Kakeya
Hideaki
H
Osada
Hiroyuki
H
D020533:Angiogenesis Inhibitors / Q000138:chemical synthesis*; D001203:Ascomycota / Q000737:chemistry; D011760:Pyrrolidinones / Q000138:chemical synthesis*; D013141:Spiro Compounds / Q000138:chemical synthesis*; D013237:Stereoisomerism
D020533:Angiogenesis Inhibitors; D011760:Pyrrolidinones; D013141:Spiro Compounds; C469812:azaspirene