Synthesis of deuterium-labeled flavanones.
Deuterium incorporation at the C-3 position of flavanones was achieved by treatment of flavanones and 2'-hydroxychalcones with D3PO4 and AcOD. We propose that the deuteration reaction mechanism for 2'-hydroxychalcones substrates is as follows. In the first step, 2'-hydroxychalcones cyclize to the corresponding flavanones by an intramolecular Michael-type reaction. Then deuteriums are incorporated into the flavanones via enolization.
Department of Organic Synthesis, School of Pharmaceutical Sciences, Kitasato UniversityTokyo 108-8641, Japan. kagawah@pharm.kitasato-u.ac.jp
Hitoshi
H
Kagawa
Tetsuya
T
Takahashi
Mariko
M
Uno
Shigeru
S
Ohta
Yoshihiro
Y
Harigaya
D002599:Chalcone / Q000031:analogs & derivatives / Q000494:pharmacology; D003903:Deuterium / Q000737:chemistry*; D044950:Flavanones / Q000138:chemical synthesis* / Q000494:pharmacology; D007536:Isomerism; D008956:Models, Chemical
D044950:Flavanones; D002599:Chalcone; D003903:Deuterium