You are here: Home :: Area NEM :: Agricultural science

Toshinari Kawada, Yuko Yoneda, Ryuji Asano, Ippei Kan-no, Walther Schmid

Synthesis of plantamajoside, a bioactive dihydroxyphenylethyl glycoside from Plantago major L.

Keywords: dihydroxyphenylethyl glycoside, glycosidation, natural products, plantamajoside, total synthesis, trichloroacetimidate, wood extractives

The first total synthesis of plantamajoside (1), 2-(3?,4?-dihydroxylphenyl)ethyl-4-O-caffeoyl-3-O-(?-D-glucopyranosyl)-?-D-glucopyranoside, which is one of the dihydroxyphenylethyl glycosides (caffeic acid sugar esters), is described. Key intermediate 2, 2-[3?,4?-bis(O-benzyl)phenyl]ethyl 2,6-di-O-acetyl-4-O-[3?,4?-bis(O-benzyl)caffeoyl]-?-D-glucopyranoside was glycosylated with trichloroacetoimidoyl 2,3,4,6-tetra-O-acetyl-?-D-glycopyranoside (3) to afford plantamajoside derivative 4a, 2-[3?,4?-bis(O-benzyl)phenyl]ethyl 2,6-di-O-acetyl-4-O-[3?,4?-bis(O-benzyl)caffeoyl]-3-O-(2,3,4,6-tetra-O-acetyl-?-D-glucopyranosyl)-?-D-glucopyranoside, in 39% yield. Plantamajoside derivative 4a was successfully converted into the target compound, plantamajoside (1), through a series of de-protective procedures. ¹H- and ¹³C nuclear magnetic resonance (NMR) spectral data of the synthesized plantamajoside (1) were identical to those of the natural compound.

Holzforschung, Walter de Gruyter

Print ISSN: 0018-3830
Volume: 60, 08/2006
Pages: 492 - 497

Show full article (external site)

Show all available items of this journal

 

Area NEM