Synthesis of oxiranylquinones as new potential bioreductive alkylating agents

Syper, Ludwik; Młochowski, J.; Kloc, K.

doi:10.1016/s0040-4020(01)91854-x

Cited by 69 publications

(53 citation statements)

References 24 publications

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“…2,4,6-pyridinetricarboxylic acid was prepared according to a literature procedure. [48] Lanthanide perchlorates were obtained as described previously. [49] Caution: Dry perchlorates and their complexes with aromatic amines may easily explode and should be handled in small quantities and with extreme caution.…”

Section: Methodsmentioning

confidence: 99%

Lanthanide Triple Helical Complexes with a Chiral Bis(benzimidazole)pyridine Derivative

Muller

Riehl

Schenk

et al. 2002

Eur. J. Inorg. Chem.

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The ligand neopentyl 2,6-bis[(1-methylbenzimidazol-2-yl)]-pyridine-4-carboxylate (L 12 ) has been synthesised to test the effect of the chiral neopentyl ester group in the 4-position of the pyridine ring on (i) the helical wrapping, (ii) the diastereomeric induction and (iii) the thermodynamic and photophysical properties of the [Ln(L 12 ) 3 ] 3+ complexes. The crystal structure of ligand L 12 shows the expected trans-trans conformation of the tridentate binding unit. The ligand forms stable 1:3 complexes in anhydrous acetonitrile (logβ 3 in the range 17.3−19.0, logK 3 in the range 2.9−4.6). The triple helical structure in solution is responsible for the four times

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Section: Methodsmentioning

confidence: 99%

Lanthanide Triple Helical Complexes with a Chiral Bis(benzimidazole)pyridine Derivative

Muller

Riehl

Schenk

et al. 2002

Eur. J. Inorg. Chem.

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“…The combined organic phase was washed with a saturated NaCl solution and dried over MgSO 4 . After evaporation under vacuum the crude product was purified over silica with 15% ether/ mL PE was dissolved 2.00 g (3.18 mmol) solanesol (22) and 5 drops pyridine. This mixture was cooled in an icebath before 0.24 mL (2.55 mmol) phosphorus tribromide was added dropwise.…”

Section: -Bromo-23-dimethyl-p-benzoquinone (5)mentioning

confidence: 99%

Synthesis and Spectroscopic Characterization of 1-13C- and 4-13C-Plastoquinone-9

et al. 2002

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Keywords: Plastoquinone-9 / Methyl butynoate / Crotononitrile / 4,4-Dimethoxy-2,3-dimethylbenzoquinone monoketal / 13 C label / Photosynthesis / Photosystem 2 / Mass spectrometry / NMR spectroscopy This paper presents the synthesis of 1-13 C-and 4-13 C-plastoquinone-9 and their characterization with NMR spectroscopy and mass spectrometry. The synthetic scheme has been further adapted to introduce 13 C-labeled plastoquinones on all individual and on each combination of positions in the qui-

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“…The cuprate activity is substrate dependent with two alkyl groups being transferred with groups such as allyl bromide and one group being transferred with bulkier substrates such as benzyl chloride, cyclohexanecarbonyl acid chloride, and benzyl bromide [19]. Syper et al [20] also utilised cuprate chemistry in the coupling of prenyl bromide and geranyl bromide to 2-bromo-3-methyl-1,4-dimethoxynaphthalene to give the protected forms of MK-1 and MK-2 in 68% and 78% respectively. A method for the preparation of MK-4 was also reported by Garcias et al [21] in 1994.…”

Section: Synthesis Of Naturally Occurring K Vitaminsmentioning

confidence: 99%