Towards the Synthesis of the Skeleton of Salvianolic Acid D

Abstract

A successful synthesis of the acid part of salvianolic acid D is described (eight steps from isovanillin, 22% overall yield). The benzaldehyde key intermediate was obtained in six steps in 52% overall yield and was converted into the trimethylated precursor molecule using the Knoevenagel procedure. Finally, the acid part of salvianolic acid D was obtained by the exhaustive deprotection of the methyl groups with boron tribromide.

Key words

natural polyphenols - antivirals - boron tribromide

References

• 1 Lu Y. Foo LY. Phytochemistry  2002,  59:  117 
• 2 Abd-Elazem IS. Chen HS. Bates RB. Huang RCC. Antiviral Res.  2002,  55:  91 
• 3 Han MK, and Lee P. inventors; WO Patent  9966942.  ; Chem. Abstr. 2000, 132, 231935
• 4 Han MK, and Lee P. inventors; US Patent  6043276.  ; Chem. Abstr. 2000, 132, 69303
• 5 Dalla V. Cotelle P. Tetrahedron Lett.  1998,  39:  8285 
• 6 Dalla V. Cotelle P. Tetrahedron  1999,  55:  6923 
• 7 Dupont R. Jeanson L. Mouscadet JF. Cotelle P. Bioorg. Med. Chem. Lett.  2001,  11:  3175 
• 8 Maurin C. Bailly F. Buisine E. Vezin H. Mbemba G. Mouscadet JF. Cotelle P. J. Med. Chem.  2004,  47:  5583 
• 9 Ai CB. Li LN. Planta Med.  1992,  58:  197 
• 10 Detterbeck R. Hesse M. Helv. Chim. Acta  2003,  86:  343 
• 11 Nicolaou KC. Seitz SP. Pavia MR. Petasis NA. J. Org. Chem.  1979,  44:  4013