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Beilstein J. Org. Chem. 2016, 12, 662–669, doi:10.3762/bjoc.12.66
Graphical Abstract
Figure 1: Structures of silibinin, isosilybin, and silychristin, and hydnocarpin-type flavonolignans.
Figure 2: Synthetic strategy of semi-synthesis of hydnocarpins from silybins [22].
Scheme 1: Synthesis of ester derivatives of silibinin and conversion to hydnocarpin-type compounds. Reaction ...
Figure 3: Putative mechanism of dehydration of flavanonols under Mitsunobu conditions.
Scheme 2: Attempt to dehydrate catechin. Reagents and conditions: a) p-nitrobenzoic acid, Ph3P, DIAD, THF, rt...
Scheme 3: Preparation of hydnocarpin (4) and isohydnocarpin (6) and attempt to dehydrate silydianin A (11). R...
Beilstein J. Org. Chem. 2015, 11, 249–264, doi:10.3762/bjoc.11.28
Figure 1: Structure of 4-hydroxybenzyl alcohol (HBA, 1).
Figure 2: Structure–activity relationship of curcumin analogs.
Scheme 1: Synthesis of curcumin (3). Reagents and conditions: (a) vanillin, 1,2,3,4-tetrahydroquinoline, HOAc...
Figure 3: Backbone and substitution of monocarbonyl analogs of curcumin (MACs) showing their structural diver...
Scheme 2: Exemplary synthesis of MAC representatives. Reagents and conditions: (a) 40% KOH, EtOH, 5 °C; stirr...
Scheme 3: Synthesis of ellagic acid (7). Reagents and conditions: (a) H2SO4, CH3OH; (b) (1) o-chloranil, Et2O...
Figure 4: Structure of resveratrol and its analogs.
Scheme 4: Synthesis of quinolone-substituted phenol 20. Reagents and conditions: (a) Ac2O, 2-hydroxybenzaldeh...
Scheme 5: Synthesis of quinolone-substituted phenol 23. Reagents and conditions: (a) Ac2O, 2-hydroxybenzaldeh...
Figure 5: Design of 4-amino-2-sulfanylphenol derivatives and their structure–activity relationship.
Scheme 6: Synthesis of 4-amino-2-sulfanylphenol derivatives. Reagents and conditions: (a) R1SO2Cl, pyridine, ...
Figure 6: Structures of two series of natural-like acylphloroglucinols.
Scheme 7: Synthesis of acylphloroglucinol derivatives 35–41. Reagents and conditions: (a) acyl chloride, AlCl3...
Scheme 8: Synthesis of acylphloroglucinol derivatives 43–51. Reagents and conditions: (a) isoprene, Amberlyst...
Figure 7: Analogs of (−)-EGCG for the prevention of oxidation and improvement of the bioavailability of the c...
Scheme 9: Synthesis of xanthohumol 58. Reagents and conditions: (a) MOMCl, diisopropylethylamine, CH2Cl2; (b)...
Scheme 10: Synthesis of genistein 60. Reagents and conditions: (a) 4-hydroxyphenylacetonitrile, anhydrous HCl,...
Scheme 11: Synthesis of fisetin (67) and quercetin (68). Reagents and conditions: (a) 3,4-dimethoxybenzaldehyd...
Figure 8: Structure of (2S)-7,2’,4’-trihydroxy-5-methoxy-8-(dimethylallyl)flavanone (69).