A short semi-synthesis and complete NMR-spectroscopic characterization of the naturally occurring lignan glycoside matairesinol 4,4'-di-O-beta-D-diglucoside.
A convenient semi-synthesis of (8R,8'R)-matairesinol 4,4'-di-O-beta-d-glucopyranoside (MDG), found in the stems of Trachelospermum asiaticum var. intermedium, is described starting from the readily available starting materials d-glucose and hydroxymatairesinol. By this approach the synthesis of MDG can be accomplished in six steps with an overall yield of 28%. In addition, the first complete NMR-spectroscopic characterization of MDG was accomplished by the combination of standard NMR techniques and spectral simulations performed with the PERCH NMR simulation software.
Ekholm
Filip S
FS
Abo Akademi University, FI-20500 Abo, Finland.
Eklund
Patrik
P
Leino
Reko
R
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D029062:Apocynaceae / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry*; D005960:Glucosides / Q000138:chemical synthesis* / Q000737:chemistry*; D017705:Lignans / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D018547:Plant Stems / Q000737:chemistry; D013237:Stereoisomerism
D001688:Biological Products; D005960:Glucosides; D017705:Lignans; C553918:matairresinol 4,4'-di-O-diglucoside; D015107:4-Butyrolactone