Highly efficient synthesis of medium-sized lactones via oxidative lactonization: concise total synthesis of isolaurepan.
A catalytic amount of TEMPO in the presence of PhI(OAc)(2) effected oxidative lactonization of 1,6- and 1,7-diols, directly affording seven- and eight-membered lactones, respectively, in good yields.
Ebine
Makoto
M
Laboratory of Biostructural Chemistry, Graduate School of Life Sciences, Tohoku University, 1-1 Tsutsumidori-amamiya, Aoba-ku, Sendai 981-8555, Japan.
Suga
Yuto
Y
Fuwa
Haruhiko
H
Sasaki
Makoto
M
D002384:Catalysis; D003497:Cyclic N-Oxides; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction
D003497:Cyclic N-Oxides; D007783:Lactones; C003959:TEMPO