Selective demethylation and debenzylation of aryl ethers by magnesium iodide under solvent-free conditions and its application to the total synthesis of natural products.
An efficient selective demethylation and debenzylation method for aryl methyl/benzyl ethers using magnesium iodide under solvent-free conditions has been developed and applied to the synthesis of natural flavone and biphenyl glycosides. A variety of functional groups including glycoside were tolerated under the reaction conditions. Experimental results indicated that the removal of an O-benzyl group was easier than that of an O-methyl group, regardless of wherever they were meta or para to the carbonyl. Thus selective debenzylation can be achieved for substrates bearing both benzyloxy and methoxy groups.
Bao
Kai
K
School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang, PR China.
Fan
Aixue
A
Dai
Yi
Y
Zhang
Liang
L
Zhang
Weige
W
Cheng
Maosheng
M
Yao
Xinsheng
X
D001554:Benzene; D001688:Biological Products / Q000138:chemical synthesis*; D004987:Ethers / Q000737:chemistry*; D006841:Hydrocarbons, Aromatic / Q000737:chemistry; D007454:Iodides / Q000737:chemistry*; D017616:Magnesium Compounds / Q000737:chemistry*; D008745:Methylation
D001688:Biological Products; D004987:Ethers; D006841:Hydrocarbons, Aromatic; D007454:Iodides; D017616:Magnesium Compounds; D001554:Benzene; C510205:magnesium iodide