Total synthesis and determination of the absolute configuration of (-)-idesolide.
The first total synthesis of (-)-idesolide was achieved via organocatalytic, enantioselective oxidative kinetic resolution (OKR) using (1S,4S)-4-Bn-1-Bu-AZADOH- and AZADO-catalyzed dimerization of (S)-(-)-methyl 1-hydroxy-6-oxo-2-cyclohexenecarboxylate. The absolute configuration of (-)-idesolide is determined to be 2R,2'S,3aS,7aR.
Yamakoshi
Hiroyuki
H
Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, Aobayama, Sendai 980-8578, Japan.
Shibuya
Masatoshi
M
Tomizawa
Masaki
M
Osada
Yuji
Y
Kanoh
Naoki
N
Iwabuchi
Yoshiharu
Y
D002384:Catalysis; D019281:Dimerization; D007700:Kinetics; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D013141:Spiro Compounds; C510160:idesolide