This work presents a literature review on the biological activity of S-carvone, geraniol and derivatives of these compounds, which are formed in the process of isomerization (during the process of geraniol isomerization, oxidation products of this compound are also obtained). Moreover, this work presents preliminary microbiological tests of creams with the addition of these biologically active compounds: S-carvone, geraniol, carvacrol (an S-carvone isomerization product), nerol (a geraniol isomerization product), linalool (a geraniol isomerization product) and citral (a geraniol oxidation product). Because the post-reaction mixture obtained after the S-carvone isomerization has a relatively simple composition, it was also added to creams and tested without isolating pure compounds. This may be a cheaper alternative to creams prepared with the addition of pure compounds. The mixture obtained after the geraniol isomerization process has a very complex composition; therefore, only compounds with the lowest molecular weight and are easily commercially available were selected for studies. The content of the tested compounds in the creams ranged from 0.5 to 3 wet%. The following microorganisms were selected for microbiological tests: the Gram-negative bacterium Escherichia coli K12, the Gram-positive bacterium Staphylococcus epidermidis, and the fungi Candida albicans, Trichophyton rubrum, Aspergillus niger, and Penicillium chrysogenum. A content of 3% carvacrol, nerol, geraniol and citral inhibited the growth of E. coli, and attenuated the growth of C. albicans and T. rubrum. On the other hand, 3% carvacrol and citral only poorly attenuated the growth of the mould fungi P. chrysogenum and A. niger.相似文献
A nickel‐catalyzed Heck cyclization for the construction of quaternary stereocenters is reported. This transformation is demonstrated in the synthesis of 3,3‐disubstituted oxindoles, which are prevalent motifs seen in numerous biologically active molecules. The method shows broad scope, proceeds in synthetically useful yields, and provides a rare means to construct stereochemically complex frameworks by nonprecious‐metal catalysis. 相似文献
The first asymmetric nickel‐catalyzed intramolecular reductive cyclization of alkynones is reported. A P‐chiral monophosphine and triethylsilane were used as the ligand and the reducing reagent, respectively, to form a series of tertiary allylic alcohols bearing furan/pyran rings in excellent yields and enantioselectivities. This reaction has a broad substrate scope and enabled the efficient synthesis of dehydroxycubebin and chiral dibenzocyclooctadiene skeletons. 相似文献
We report herein an efficient gold(I)‐catalyzed post‐Ugi domino dearomatization/ipso‐cyclization/Michael sequence that enables access to libraries of diverse (hetero)arene‐annulated tricyclic heterocycles. This process affords novel complex polycyclic scaffolds in moderate to good yields from readily available acyclic precursors with excellent chemo‐, regio‐, and diastereoselectivity. The power of this strategy has been demonstrated by the rapid synthesis of 40 highly functionalized polyheterocycles bearing indole, pyrrole, (benzo)furan, (benzo)thiophene, pyrazole, and electron‐rich arene groups in two operational steps. 相似文献
Polyene cyclizations offer rapid entry into terpenoid ring systems. Although enantioselective cyclizations of (E)‐polyenes to form trans‐decalin ring systems are well precedented, highly enantioselective cyclizations of (Z)‐polyenes to form the corresponding cis‐decalins have not been reported. Here, we describe the first application of iminium catalysis to the initiation of polyene cyclizations. Ethyl 1,2‐diazepane‐1‐carboxylate catalyzes the cyclization of polyenes bearing enal initiators. Moreover, chiral bicyclic hydrazides catalyze the cyclizations of (Z)‐polyene substrates to form cis‐decalins with enantioselectivities of up to 97:3 er. DFT calculations suggest the catalysts promote the reaction by stabilizing positive charge as it develops during the bicyclization. 相似文献
A review of the polycyclization reaction of the C35 polyprenoid by squalene‐hopene cyclase: Surprisingly, our results completely disagree with a previous publication in which it was reported that a hexacyclic skeleton was constructed as the single product. In our work many tri‐ and tetracyclic scaffolds were isolated, but no penta‐ or hexacycles. The reasons for the different results and the mechanism of the polycyclization reaction are discussed (see figure).
A novel enantioselective palladium‐catalyzed dearomative cyclization has been developed for the efficient construction of a series of chiral phenanthrenone derivatives bearing an all‐carbon quaternary center. The effectiveness of this method in the synthesis of terpenes and steroids was demonstrated by a highly efficient synthesis of a kaurene intermediate, the facile construction of the skeleton of the anabolic steroid boldenone, and the enantioselective total synthesis of the antimicrobial diterpene natural product (?)‐totaradiol. 相似文献
A silver triflate‐catalyzed electrophilic cyclization reaction of acyclic triynols with NXS (X=I, Br) under mild conditions is reported. Three reactive functional groups, such as a carbonyl group, an alkyne group, and a halogen, could be selectively installed at the C1, C2, and C3 positions to obtain the naphthalene and quinoline products, respectively. The obtained densely trisubstituted products could be further transformed into more complex aromatic products by manipulating the alkynyl moiety and the other two functional groups as synthons. 相似文献
The factors that control the chemoselectivity of palladium‐catalyzed cyclization reactions of (2‐iodoanilino)carbonyl compounds have been explored by an extensive experimental computational (DFT) study. It was found that the selectivity of the process, that is, the formation of fused six‐ versus five‐membered rings, can be controlled by the proper selection of the initial reactant, reaction conditions, and additives. Thus, esters or amides produce ketones by a nucleophilic addition process, whereas the addition of PhO? ions leads to the formation of indolines by an α‐arylation reaction. In contrast, the corresponding ketone reactants yield a mixture of both reaction products, the ratio of which depends on the base used, in the presence of phenol. The outcome of the processes can be explained by the formation of a common four‐membered palladacycle intermediate from which the competitive nucleophilic addition and α‐arylation reactions occur. The remarkable effect of phenol in the process, which makes the α‐arylation reaction easier, favored the formation of enol complexes, which are stabilized by an intramolecular hydrogen bond between the hydroxy group of the enol moiety and the oxygen atom of the phenoxy ligand. Moreover, the chemoselectivy of the process can be also controlled by the addition of bidendate ligands that lead to the almost exclusive formation of indoles at expenses of the corresponding alcohols. 相似文献
The present work was undertaken to determine liquid–liquid equilibria for ternary systems involved in the citrus essential oil terpeneless using dilute alcohol. Tie-line data have been determined for the linalool + ethanol + water, water + ethanol + limonene, and limonene + linalool + water ternary systems at 298.15 K. The experimental data were satisfactorily correlated using the UNIQUAC and NRTL equations, and the obtained binary interaction parameters are reported. The UNIFAC group-contribution method did not allow adequate predictions of liquid–liquid equilibria involved in this study. 相似文献
Based on stereoisotopic studies and β‐secondary isotope effects, we propose that the acid‐catalyzed cyclization of geranyl acetate proceeds through a concerted mechanism. Under heterogeneous conditions (zeolite Y confinement), a preorganized chairlike transition state predominates, whereas under homogeneous conditions the boat‐ and chairlike transition states are almost isoenergetic. For the case of farnesyl acetate, we propose that under homogeneous conditions a concerted dicyclization occurs with a preorganized boat–chair transition state competing with the chair–chair transition state. Under zeolite confinement conditions, the chair–chairlike dicyclization transition state is highly favorable. The preference of chairlike transition states within the cavities of zeolite Y is attributed to a transition state shape selectivity effect. 相似文献
A novel N‐heterocyclic carbene (NHC)‐palladium‐catalyzed three‐component cascade cyclization/alkynylation for the synthesis of structurally diverse 4‐alkynylisoxazoles was efficiently developed in ionic liquids. The operational simplicity, without additives, no additional ligands, and 0.5 mol % catalyst loading under air are some of the attractive features of this present protocol. 相似文献