2005
DOI: 10.1016/j.tet.2004.12.061
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Synthesis and structural revision of naturally occurring ayapin derivatives

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Cited by 45 publications
(25 citation statements)
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“…45) Aromatic aldehyde 1 was obtained from sesamol by the reaction of Vilsmeier-Haack formylation in 11% yield. 46) 1,3-Benzodioxole reacted with paraformaldehyde in a concentrated HCl solution to provide 2, 47) and followed by treatment with bromine in glacial acetic acid to yield 4 in 92% yield. 48) Compounds 2 and 4 were oxidized by dimethylsulphoxide oxidation in the presence of NaHCO 3 to yield intermediates 3 and 5, respectively.…”
Section: Resultsmentioning
confidence: 99%
“…45) Aromatic aldehyde 1 was obtained from sesamol by the reaction of Vilsmeier-Haack formylation in 11% yield. 46) 1,3-Benzodioxole reacted with paraformaldehyde in a concentrated HCl solution to provide 2, 47) and followed by treatment with bromine in glacial acetic acid to yield 4 in 92% yield. 48) Compounds 2 and 4 were oxidized by dimethylsulphoxide oxidation in the presence of NaHCO 3 to yield intermediates 3 and 5, respectively.…”
Section: Resultsmentioning
confidence: 99%
“…199.5°C; 1 H-NMR δ (CDCl 3 ): 6.07 (2H, s), 6.28 (1H, d, J=9. The structure of compounds (2-6) were elucidated and confirmed by 1 H and 13 C-NMR, MS, and by subsequent comparisons with reference data from the available literature (Duddeck and Kaiser 1982;Tsukamoto et al 1984;Afek et al 1986;Debenedetti et al 1998;Maes et al 2005).…”
Section: Synthesis Procedures and Spectral Data Of Coumarinmentioning
confidence: 91%
“…In our previous chemical investigations of this plant, sesquiterpene lactones and flavonoids have been identified as constituents of the plant [4]. In the course of our continuing search for this plant, nine compounds were isolated and identified as isofraxidin(1), 8-methoxy-6,7-methylenedioxy-coumarin(2), 7-methylnaringenin(3), kaemferol(4), kaemferol-3-O-rhamno-pyranosyl (1→6) glucopyranoside (5), eleutheroside B 1 (6), isofraxidin-7-Oβ -D-xylopyranosyl(1-3)α -D-glucopyranoside (7), rosmarinic acid (8), 3,4-dihydroxyphenethyl caffeate (9). Here we report the isolation and structure elucidation of these compounds.…”
Section: Introductionmentioning
confidence: 99%