58402-11-2Relevant academic research and scientific papers
Total synthesis of Cannabisin B
Xia, Yamu,Zhang, Huaizheng,Li, Chenchen,Dong, Gaochao,Liu, Zhen
, p. 606 - 608 (2015)
Cannabisin B, a naturally occurring lignanamide, has been synthesised for the first time in 15% overall yield. The convergent synthesis is based on the Stobbe reaction and Friedel-Crafts alkylation reaction as the C-C bond-forming steps to afford the skel
Total synthesis of leoligin from edelweiss roots
Xia, Yamu,Zou, Lijia,Zhang, Jiahong,Zhang, Wen
, p. 350 - 353 (2018/08/21)
Leoligin, a tetrahydrofuran lignan isolated from the root of the edelweiss plant, was synthesised from veratraldehyde (2 mol), diethyl succinate and 2-methyl-(Z)-2-butenoic acid. Initially, veratraldehyde and diethyl succinate underwent a Stobbe condensation to yield a C6-C5 acid which, after esterification, was condensed with a second molecule of veratraldehyde to generate a 2,3,4-trisubsituted γ-butyrolactone intermediate. Two reduction steps yielded a triol, which was ring-closed with tosyl chloride to form a hydroxymethyl-tetrahydrofuran, esterification of which with 2-methyl-(Z)-2-butenoic acid generated leoligin.
Antiproliferative and apoptotic effects of the oxidative dimerization product of methyl caffeate on human breast cancer cells
Bailly, Fabrice,Toillon, Robert-Alain,Tomavo, Olympe,Jouy, Nathalie,Hondermarck, Hubert,Cotelle, Philippe
, p. 574 - 578 (2013/02/26)
Caffeic acid derivatives are increasingly regarded as potential oncoprotective that could inhibit both the initiation and progression of cancer. Here we have synthesized seven 1-arylnaphthalene lignans and related compounds and tested their impact on breast cancer cell growth in tissue culture. The product of the oxidative dimerization of methyl caffeate, 1-phenylnaphthalene lignan, was found to induce a strong decrease in breast cancer cell number (IC50 ～1 μM) and was selected for further investigation. Flow cytometry analysis revealed a decrease in cell proliferation and an increase in apoptosis in both MCF-7 and MDA-MB-231 breast cancer cell lines that are representative of the two main categories of breast tumors. The 3,4-dihydroxyphenyl group probably induced the biological activity, as the control compounds lacking it had no effect on breast cancer cells. Together, our data indicate that the oxidative dimerization product of methyl caffeate can inhibit breast cancer cell growth at a concentration adequate for pharmacological use.
Synthesis, anti-virus and anti-tumour activities of dibenzylbutyrolactone lignans and their analogues
Xia, Yamu,You, Jia,Zhang, Yuanyuan,Su, Zhongliang
experimental part, p. 565 - 569 (2010/03/03)
An efficient synthesis of dibenzylbutyrolactone lignans and their analogues has been developed. Based on a Stobbe condensation of piperonal or veratraldehyde with diethylsuccinate and alkylation with 3,4- methylenedioxybenzyl bromide to give the skeleton
Antiviral activity of arylnaphthalene and aryldihydronaphthalene lignans
Cow, Christopher,Leung, Carmen,Charlton, James L.
, p. 553 - 561 (2007/10/03)
A practical method for large scale synthesis of 1- arylnaphthalene and 1-aryl-1,2-dihydronaphthalene lignans is described. The method makes use of the classic Stobbe condensation followed by regioselective reactions that provide access to both the common
