55009-70-6Relevant academic research and scientific papers
Synthesis and biological evaluation of bilobol and adipostatin A
Tanaka, Ayano,Arai, Yasuhiro,Kim, Su-Nam,Ham, Jungyeob,Usuki, Toyonobu
, p. 290 - 296 (2011/06/19)
Concise total synthesis of bilobol 5-pentadecenylresorcinol (1), isolated from Gingko biloba fruits, has been achieved in 10 steps with 51% overall yield from 3,5-dihydroxybenzoic acid (3). Adipostatin A (2), isolated from the fruits as well as from Streptomyces cyaneus 2299-SV1, has also been synthesized in two steps from methylated bilobol (10). The structure-activity relationship study of synthetic products was described by means of cytotoxic assay against human KB carcinoma cell lines.
5-Alkylresorcinols from Hakea trifurcata that cleave DNA
Lytollis, William,Scannell, Ralph T.,An, Haoyun,Murty,Reddy, K. Sambi,Barr, John R.,Hecht, Sidney M.
, p. 12683 - 12690 (2007/10/03)
A dichloromethane extract of Hakea trifurcata that mediated relaxation of ?X174 replicative form DNA at micromolar concentrations in the presence of Cu2+ was resolved into six active components by bioassay-guided fractionation. Five of the acti
Long Chain Phenols. Part 17. The Synthesis of 5-resorcinol, 'Cardol monoene,' and of 5-resorcinol Dimethyl Ether, 'Cardol diene' Dimethyl Ether
Baylis, Christopher J.,Odle, Stanley W.,Tyman, John H. P.
, p. 132 - 141 (2007/10/02)
Two unsaturated compounds in the 'cardol' series, an important component phenol from Anacardium Occidentale, have been synthesised. 3,5-Dimethoxybenzaldehyde interacted with OH-protected 6-chlorohexan-1-ol in the presence of lithium to give, after acidic treatment, 1-(3,5-dimethoxyphenyl)heptane-1,7-diol which was hydrogenolysed selectively to 7-(3,5-dimethoxyphenyl)heptan-1-ol.Conversion into the bromide and alkylation of lithio-oct-1-yne gave 5-(pentadec-8-ynyl)resorcinol dimethyl ether which was selectively converted into the 8-(Z)-alkene.Dmethylation with lithium iodide gave 5-resorcinol which was identical to 'cardol monoene'.Reaction of 7-(3,5-dimethoxyphenyl)heptyl bromide with lithium derivative of OH-protected propargyl alcohol, gave after acidic treatment 10-(3,5-dimethoxyphenyl)dec-2-yn-1-ol, the bromide of which with pent-1-ynylmagnesium bromide afforded 5-pentadec-8,11-diynylresorcinol dimethyl ether.Selective hydrogenation yielded 5-resorcinol dimethyl ether identical with the dimethyl ether of 'cardol diene.'
