Abstract
An efficient method for the synthesis of apigenin (4’,5,7-trihydroxyflavone, a traditional medicine) from phloroglucinol and anisaldehyde has been developed. This transformation features a green method for hydroxyl protection as methyl ethers and a different way for cyclisation using iodine in DMSO. The overall yield of 40% is satisfactory.
References
1.
Trichopoulou A.
,
Vasilopoulou E.
, and
Hollman P.
, Food Chem. , 2000 , 70 , 319 .
2.
Justesen U.
, and
Knuthsen P.
, Food Chem. , 2001 , 73 , 245 .
3.
Liu T.
, and
Hu Y.Z.
, Synth. Commun. , 2004 , 34 , 3209 .
4.
Yeole P.G.
,
Wadher S.J.
, and
Gaikwad N.J.
, Int. J. Chem. Sci. , 2007 , 5 , 1133 .
5.
Seijas J.A.
,
Vazquez-Tato M.P.
, and
Carballido-Reboredo R.
, J. Org. Chem. , 2005 , 70 , 2855 .
6.
Wei G.
, and
Yu B.
, Eur. J. Org. Chem. , 2008 , 18 , 3156 .
7.
Shaw A.Y.
,
Chang C.-Y.
,
Liau H.-H.
,
Lu P.-J.
,
Chen H.-L.
,
Yang C.-N.
, and
Li H.-Y.
, Eur. J. Med. Chem. , 2009 , 44 , 2552
8.
Smith J.A.
,
Maloney D.J.
,
Hecht S.M.
, and
Lannigan D.A.
, Bioorg. Med. Chem. , 2007 , 15 , 5018
9.
Wang J.
,
Yang J.
,
Yang B.
,
Hu X.
,
Sun J.-Q.
, and
Yang T.
, J. Chem. Res. , 2010 , 34 , 717 .
10.
Wang J.
,
Yang J.
,
Yang B.
,
Sun J.-Q.
, and
Yang T.
, J. Chem. Res. , 2010 , 34 , 724 .
11.
Wang J.
,
Yang J.
,
Zhou R.-G.
,
Yang B.
, and
Wu Y.-S.
, J. Chem. Res. , 2011 , 35 , 428 .
12.
Wang J.
,
Yang J.
,
Zhou R.-G.
,
Yang B.
, and
Wu Y.-S.
, J. Chem. Res. , 2011 , 35 , 431 .
13.
Bringmann G.
,
Noll T.F.
,
Gulder T.
,
Dreyer M.
,
Grune M.
, and
Moskau D.
, J. Org. Chem. , 2007 , 72 , 3247
14.
Chu H.-W.
,
Wu H.-T.
, and
Lee Y.-J.
, Tetrahedron , 2004 , 60 , 2647