Synthesis of the glycosidic precursor of isomeric marmelo lactones, volatile components of the quince fruit, Cydonia oblonga.
The glucosidic precursor of marmelo lactones was synthesized by employing a common intermediate which had been used for the synthesis of the glucosidic precursor of marmelo oxides. The synthesis was performed by modifying the former procedure. Monochloroacetyl was adopted to protect both the glucose and aglycon hydroxyl groups for selective transesterification in the presence of the glycosyl ester. Glycosylation of the aglycon carboxyl group with 1-alpha-bromopermonochloroacetylglucose and final selective alcoholysis yielded the target glucoside.
Shimizu
Hiroki
H
Department of Applied Biological Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo, Japan.
Kitahara
Takeshi
T
D006027:Glycosides / Q000096:biosynthesis*; D006031:Glycosylation; D007536:Isomerism; D007783:Lactones / Q000737:chemistry* / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D015394:Molecular Structure; D027824:Rosaceae / Q000378:metabolism*
D006027:Glycosides; D007783:Lactones