“…On the basis of NMR, the structures of all synthesized molecules were determined (Figure S1). Singlet signals with chemical shifts in the range of 7.67-7.41 ppm (s, 1H) and 137.3-130.0 ppm for 1 H and 13 C spectra, respectively, were observed in the 1 H spectrum of synthetic compounds 2-9 and were attributed to the presence of typical transolefinic proton, corresponding to the bond between the cycloalkanone and the aromatic ring, values that are in agreement with those previously reported for this family of compounds [24,30,31]. These data were corroborated for all the molecules using the heteronuclear multiple-bond correlation (HMBC) spectra.…”
The aim of this study was to synthesize a series of novel and known dihydrocarvone-hybrid derivatives (2–9) and to evaluate mycelial growth activity of hybrid molecules against two strains of Monilinia fructicola, as well as their toxicity. Dihydrocarvone-hybrid derivatives have been synthesized under sonication conditions and characterized by FTIR, NMR, and HRMS. Antifungal efficacy against both strains of M. fructicola was determined by half maximal effective concentration (EC50) and toxicity using the brine shrimp lethality test (BSLT). Among the synthesized compounds, 7 and 8 showed the best activity against both strains of M. fructicola with EC50 values of 148.1 and 145.9 µg/mL for strain 1 and 18.1 and 15.7 µg/mL for strain 2, respectively, compared to BC 1000® (commercial organic fungicide) but lower than Mystic® 520 SC. However, these compounds showed low toxicity values, 910 and 890 µg/mL, respectively, compared to Mystic® 520 SC, which was highly toxic. Based on the results, these hybrid compounds could be considered for the development of more active, less toxic, and environmentally friendly antifungal agents against phytopathogenic fungi.
“…On the basis of NMR, the structures of all synthesized molecules were determined (Figure S1). Singlet signals with chemical shifts in the range of 7.67-7.41 ppm (s, 1H) and 137.3-130.0 ppm for 1 H and 13 C spectra, respectively, were observed in the 1 H spectrum of synthetic compounds 2-9 and were attributed to the presence of typical transolefinic proton, corresponding to the bond between the cycloalkanone and the aromatic ring, values that are in agreement with those previously reported for this family of compounds [24,30,31]. These data were corroborated for all the molecules using the heteronuclear multiple-bond correlation (HMBC) spectra.…”
The aim of this study was to synthesize a series of novel and known dihydrocarvone-hybrid derivatives (2–9) and to evaluate mycelial growth activity of hybrid molecules against two strains of Monilinia fructicola, as well as their toxicity. Dihydrocarvone-hybrid derivatives have been synthesized under sonication conditions and characterized by FTIR, NMR, and HRMS. Antifungal efficacy against both strains of M. fructicola was determined by half maximal effective concentration (EC50) and toxicity using the brine shrimp lethality test (BSLT). Among the synthesized compounds, 7 and 8 showed the best activity against both strains of M. fructicola with EC50 values of 148.1 and 145.9 µg/mL for strain 1 and 18.1 and 15.7 µg/mL for strain 2, respectively, compared to BC 1000® (commercial organic fungicide) but lower than Mystic® 520 SC. However, these compounds showed low toxicity values, 910 and 890 µg/mL, respectively, compared to Mystic® 520 SC, which was highly toxic. Based on the results, these hybrid compounds could be considered for the development of more active, less toxic, and environmentally friendly antifungal agents against phytopathogenic fungi.
“…[11] In contrast, transforming 6 into 8 required an additional 1,2-carbonyl shift, [12] which was achieved in six steps with a good overall yield of 57 %. An initial aldol condensation of 6 with benzaldehyde (tBuOK, tBuOH, reflux) [13] caused a partial epimerization a to the carbonyl group, which was avoided by using a sequence consisting of a kinetically controlled deprotonation, [14] an aldol reaction with benzaldehyde, and subsequent elimination. [15] Removal of the keto functionality from the molecule was accomplished by reduction [16] to give the allyl alcohol 9, esterification to provide the corresponding carbonate 10, [17] and palladium-catalyzed reduction of 10 using triethylamine and formic acid to yield 11.…”
Let it rip: An intramolecular Diels–Alder reaction and two intramolecular aldol condensations allow the efficient preparation of the title compound 2, a close analogue of the diterpene 1 which was isolated from the defense secretion of termite soldiers. The synthesis commenced with cyclohexanone 3, which is rapidly available from (−)‐isopulegol.
“…Synthesis of Aldol Condensation Products. The products from the aldol condensation, the α,β-unsaturated ketones 3a and 3b , were synthesized for use in the establishment of assays and as standards for polymer−ligand recognition studies, using an adaption of the procedure described by Chuiko et al Enantiomerically pure camphor, 1a or 1b , was reacted with benzaldehyde ( 2 ) in the presence of n -BuLi in DMSO to furnish the corresponding ketone, 3a or 3b , though in low yield (Scheme ). 4 Synthesis of Ketone 3 a from ( S )-Camphor ( 1 a ) a a Ketone 3b was synthesized from 1b in the same manner. …”
[structures: see text] A class II aldolase-mimicking synthetic polymer was prepared by the molecular imprinting of a complex of cobalt (II) ion and either (1S,3S,4S)-3-benzoyl-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one (4a) or (1R,3R,4R)-3-benzoyl-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one (4b) in a 4-vinylpyridine-styrene-divinylbenzene copolymer. Evidence for the formation of interactions between the functional monomer and the template was obtained from NMR and VIS titration studies. The polymers imprinted with the template demonstrated enantioselective recognition of the corresponding template structure, and induced a 55-fold enhancement of the rate of reaction of camphor (1) with benzaldehyde (2), relative to the solution reactions, and were also compared to reactions with a series of reference polymers. Substrate chirality was observed to influence reaction rate, and the reaction could be competitively inhibited by dibenzoylmethane (6). Collectively, the results presented provide the first example of the use of enantioselective molecularly imprinted polymers for the catalysis of carbon-carbon bond formation.
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