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Synthesis of deacetyl-1,10-didehydrosalvinorin G.

ABSTRACT: To unambiguously confirm the actual product in autoxidation of salvinorin A under basic conditions, deacetyl-1,10-didehydrosalvinorin G was synthesized from salvinorin C via intermediate salvinorin H. Furthermore, oxidation of salvinorin D with manganese dioxide gave salvinorin G in good yield.

SUBMITTER: Ma Z

PROVIDER: S-EPMC2390901 | biostudies-literature | 2008 Mar

REPOSITORIES: biostudies-literature

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Synthesis of deacetyl-1,10-didehydrosalvinorin G.

Ma Zhongze Z Lee David Y W DY

Tetrahedron letters 20080301 11

To unambiguously confirm the actual product in autoxidation of salvinorin A under basic conditions, deacetyl-1,10-didehydrosalvinorin G was synthesized from salvinorin C via intermediate salvinorin H. Furthermore, oxidation of salvinorin D with manganese dioxide gave salvinorin G in good yield. ...[more]

PMID: 19279674

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Revised structure of deacetyl-1,10-didehydrosalvinorin G.

Project description:In comparison with the NMR data of salvinorin A and its 8-epimer, the published structure of deacetyl-1,10-didehydrosalvinorin G was revised to its 8-epimer. The stereochemistry of 8-epi-deacetyl-1,10-didehydrosalvinorin G was further confirmed by NOESY and chemical synthesis.

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7-Deacetyl-gedunin.

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Deacetyl-nomilin monohydrate.

Project description:In the title compound (systematic name 1-hy-droxy-1,2-dihydro-obacunoic acid 3,4-lactone monohydrate), C(26)H(32)O(8)·H(2)O, the dihedral angles between the planes of the ester groups and the furan plane are 43.06?(12) and 56.06?(7)°, while that between the furan plane and the keto group is 58.50?(9)°. The A/B, B/C and C/D ring junctions are all trans-fused. Inter-molecular O-H?O hydrogen bonds between the hy-droxy and carbonyl groups and the water mol-ecule give rise to a three-dimensional structure.

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Deacetyl- tenuazonic acid.

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Deacetyl tenuazonic acid p-toluene-sulfonyl-hydrazone.

Project description:The title compound {systematic name: 4-methyl-N'-[(3E)-2-(1-methyl-prop-yl)-5-oxopyrrolidin-3-yl-idene]benzene-sulfono-hydrazide}, C(15)H(21)N(3)O(3)S, is the condensation product of deacetyl tenuazonic acid (DTA) and p-toluene-sulfonohydrazide. The crystal structure consists of chains along [100] linked by N-H⋯O hydrogen bonds.

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Synthesis and Characterization of 1,10-Phenanthroline-mono-<i>N</i>-oxides.

Project description:N-oxides of N-heteroaromatic compounds find widespread applications in various fields of chemistry. Although the strictly planar aromatic structure of 1,10-phenanthroline (phen) is expected to induce unique features of the corresponding N-oxides, so far the potential of these compounds has not been explored. In fact, appropriate procedure has not been reported for synthesizing these derivatives of phen. Now, we provide a straightforward method for the synthesis of a series of mono-N-oxides of 1,10-phenanthrolines. The parent compounds were oxidized by a green oxidant, peroxomonosulfate ion in acidic aqueous solution. The products were obtained in high quality and at good to excellent yields. A systematic study reveals a clear-cut correlation between the basicity of the compounds and the electronic effects of the substituents on the aromatic ring. The UV spectra of these compounds were predicted by DFT calculations at the TD-DFT/TPSSh/def2-TZVP level of theory.

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Synthesis of N-Tetradecyl-1,10-phenathrolinium-Based New Salts for Biological Applications.

Project description:New organic salts were synthesized by quaternizing 1,10-phenanthroline using 1-bromotetradecane. The first step yielded an organic salt of formula [C26H37N2]Br. Anion exchange reaction using Li[(CF3SO2)2N] resulted in a more stable salt of formula [C26H37N2][(CF3SO2)2N]. The organic salts were investigated by spectrometry (1H, 13C, 19F NMR, X-ray photoelectron spectroscopy (XPS), UV-Vis, and matrix-assisted laser desorption/ionization mass spectroscopy (MALDI MS), CHNSBr elemental analysis, and thermal analysis (TGA and DSC). The thermal characterization showed the melting and decomposition points of [C26H37N2][(CF3SO2)2N] to be 48°C and 290°C, respectively, which indicates it is an ionic liquid with large liquidus range. The biological activities of the salts were investigated against two Gram-positive (Staphylococcus aureus and Streptococcus pyogenes) and two Gram-negative (Escherichia coli and Klebsiella pneumoniae) bacteria, and they are found to be active against all of them. They were compared with [Cu(1,10-phenanthroline)2Cl]Cl. They are found more active against the Gram-negative bacteria. The salts demonstrated minimum inhibitory concentration as low as 50 µg/L. These results suggest the synthesized salts can be considered as a better alternative to certain transition metal complex drugs. This minimizes the concern of introducing metal ions into the organism.

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Palladium(II) complexes of 1,10-phenanthroline: Synthesis and X-ray crystal structure determination.

Project description:Two palladium(II) complexes, [Pd(phen)(N identical withCCH(3))(2)][O(3)SCF(3)](2) (1) and [Pd(phen)(mu-OH)](2)[O(3)SCF(3)](2).2H(2)O (2) (where phen= 1,10-phenanthroline), have been crystallized following the reaction of Pd(phen)Cl(2) with silver triflate, Ag(O(3)SCF(3)), in acetonitrile and water, respectively. The structures of both complexes are based on a Pd(phen)(2+) metal core, with two acetonitrile molecules binding in a monodentate fashion in complex 1 and two hydroxo bridges holding together two cores to form a dimer in complex 2. Additionally, both complexes present a hydrogen bonded 3-D network involving the triflate anions in 1, and water and triflate anions in 2. Both complexes have been characterized by infrared and (1)H NMR spectroscopy and their crystal structures determined by X-ray crystallography.

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Synthesis and Electrochemical and Spectroscopic Characterization of 4,7-diamino-1,10-phenanthrolines and Their Precursors.

Project description:New approaches to the synthesis of 4,7-dichloro-1,10-phenanthrolines and their corresponding 9H-carbazol-9-yl-, 10H-phenothiazin-10-yl- and pyrrolidin-1-yl derivatives were developed. Their properties have been characterized by a combination of several techniques: MS, HRMS, GC-MS, electronic absorption spectroscopy and multinuclear NMR in both solution and solid state including 15N CP/MAS NMR. The structures of 5-fluoro-2,9-dimethyl-4,7-di(pyrrolidin-1-yl)-1,10-phenanthroline (5d), 4,7-di(9H-carbazol-9-yl)-9-oxo-9,10-dihydro-1,10-phenanthroline-5-carbonitrile (6a) and 4,7-di(10H-phenothiazin-10-yl)-1,10-phenanthroline-5-carbonitrile (6b) were determined by single-crystal X-ray diffraction measurements. The nucleophilic substitutions of hydrogen followed by oxidation produced compounds 6a and 6b. The electrochemical properties of selected 1,10-phenanthrolines were investigated using cyclic voltammetry and compared with commercially available reference 1,10-phenanthrolin-5-amine (5l). The spatial distribution of frontier molecular orbitals of the selected compounds has been calculated by density functional theory (DFT). It was shown that potentials of reduction and oxidation were in consistence with the level of HOMO and LUMO energies.

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Synthesis and Spectroscopic Characterization of Selected Water-Soluble Ligands Based on 1,10-Phenanthroline Core.

Project description:Water-soluble ligands based on a 1,10-phenanthroline core are relatively poorly studied compounds. Developing efficient and convenient syntheses of them would result in new interesting applications because of the importance of 1,10-phenanthrolines. In this manuscript, we describe novel and practical ways to introduce a carboxyl and, for the first time, a phenol and dithiocarboxyl group under mild reaction conditions. This strategy enables highly efficient and practical synthesis of suitable organosulfur compounds with high added value, high chemoselectivity, and a broad substrate range. We present the selective conversion of a hydroxydialdehyde in the form of 10-hydroxybenzo[h]quinoline-7,9-dicarbaldehyde into its derivative, unique hydroxydicarboxylic acid, by an oxidation procedure, giving 10-hydroxybenzo[h]quinoline-7,9-dicarboxylic acid. A similar procedure resulted in the formation of 9-methyl-1,10-phenanthroline-2-carboxylic acid by oxidation of commercially available neocuproine. An alternative method of obtaining 1,10-phenanthroline derivatives possessing carboxylic acid group can be based on the hydrolysis of ester or nitrile groups; however, this synthesis leads to unexpected products. Moreover, we apply Perkin condensation to synthesize a vinyl (or styryl) analog of 1,10-phenanthroline derivatives with phenol function. This reaction also demonstrates a new, simple, and efficient strategy for converting methyl derivatives of 1,10-phenanthroline. We anticipate that the new way of converting methyl will find wide application in chemical synthesis.

| S-EPMC10975036 | biostudies-literature

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