Enantioselective syntheses of aeruginosin 298-A and its analogues using a catalytic asymmetric phase-transfer reaction and epoxidation.
We developed a versatile synthetic process for aeruginosin 298-A as well as several attractive analogues, in which all stereocenters were controlled by a catalytic asymmetric phase-transfer reaction and epoxidation. Furthermore, drastic counteranion effects in phase-transfer catalysis were observed for the first time, making it possible to three-dimensionally fine-tune the catalyst (ketal part, aromatic part, and counteranion).
Ohshima
Takashi
T
Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Gnanadesikan
Vijay
V
Shibuguchi
Tomoyuki
T
Fukuta
Yuhei
Y
Nemoto
Tetsuhiro
T
Shibasaki
Masakatsu
M
D002384:Catalysis; D004852:Epoxy Compounds / Q000737:chemistry*; D007930:Leucine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure
D004852:Epoxy Compounds; C419325:aeruginosin 298-A; D007930:Leucine