4,6-Dimethoxy-3,7-dimethylcoumarin from Colchicum decaisnei. Total synthesis by carbamoyl Baker-venkataraman rearrangement and structural revision to isoeugenetin methyl ether
Structures 1 has been revised to 2a, a derivative of 2b, isolated from Eugenia caryophyllata
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Cited by (34)
Nickel-Catalyzed Decarbonylative Cycloaddition of Benzofuran-2,3-diones with Alkynes to Flavones
2022, Advanced Synthesis and CatalysisAcylphloroglucinol derivatives from the leaves of Syzygium samarangense and their cytotoxic activities
2018, FitoterapiaCitation Excerpt :In the HMBC spectrum of 3, the observed correlations between 8-CH3 (δH 2.19) and C-7 (δC 160.6)/C-9 (δC 155.9), as well as between H-3 (δH 6.04) and C-10 (δC 105.1) allowed the establishment of a 5,7-dihydroxy-8-methyl chromone moiety in 3 instead of the 5,7-dihydroxy-6,8-dimethyl chromone unit in 2. The above determination was further confirmed by comparison the NMR data assigned to the chromone moiety of 3 with those reported in the literature [26]. Further analysis of the 2D NMR data of 3 indicated that 3 had the same linear C17 alkyl side chain as that of 2.
Scale-up of one-step synthesis of acacetin and apigenin using 915 MHz microwaves
2017, Chemical Engineering and Processing - Process IntensificationCitation Excerpt :Moreover, the quality and quantity of the extracted metabolite are generally dependent on the raw material sources: crop type, harvest place and period, preservation, extraction process, etc. By chemical synthesis, flavones have been largely synthesized via Allan Robinson reaction [12–14], Baker-Venkataraman rearrangement [15–19], acidic cyclization of chalcones [20], synthesis from flavonols obtained via Auwers synthesis [21], and Algar-Flynn-Oyamada reaction [22]. As far as the synthetic apigenin, numerous dealkylation methods starting from acacetine are described in the literature; amongst them dealkylation with HI, Me3SiI, BBr3 in DCM, AlCl3 in toluene or reflux in HBr, AcOH with HCl [23–29].
Induced production of novel prenyldepside and coumarins in endophytic fungi Pestalotiopsis acaciae
2013, Tetrahedron Letters