Stereochemie von Metallocenen, 14. Mit.: Chemische Korrelation und absolute Konfiguration von optisch aktiven α- und β-substituierten Methylcymantrenen

Gowal, Heike; Schlögl, K.

doi:10.1007/bf00908929

Cited by 12 publications

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“…Carboxylic acid 9 was prepared following a literature procedure . Reduction of the keto group of 9 using Zn(Hg) and concentrated HCl (Clemmensen reduction) gave 10 in 73% yield. − The cymantrene fused cyclohexenone 11 was prepared by polyphosphoric acid mediated intramolecular cyclization of 10 . Afterward a synthetic route similar to that developed previously during our synthesis of C6–C7 ferrocene fused platensimycin derivative 3 was applied to synthesize the C6–C7 cymantrene fused platensimycin derivative 4 from 11 .…”

Section: Resultsmentioning

confidence: 99%

“…32−34 The cymantrene fused cyclohexenone 11 was prepared by polyphosphoric acid mediated intramolecular cyclization of 10. 34 Afterward a synthetic route similar to that developed previously during our synthesis of C6−C7 ferrocene fused platensimycin derivative 3 was applied to synthesize the C6− C7 cymantrene fused platensimycin derivative 4 from 11. 30 Treatment of 11 with KHMDS and MeI gave exclusively the exo-methylated ketone 12 in 62% yield.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…1 Cyclic Ketone 11. 34 A mixture of 10 (300 mg, 1.03 mmol) and polyphosphoric acid (8 g) was heated at 80 °C for 7 h. Water was added to the reaction mixture, and this mixture was extracted with Et 2 O (2 × 50 mL). The organic phase was washed with 1 M HCl (1 × 30 mL), water (5 × 50 mL), and brine (1 × 30 mL), dried over Na 2 SO 4 , and filtered.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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Sandwich and Half-Sandwich Derivatives of Platensimycin: Synthesis and Biological Evaluation

et al. 2012

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The multistep synthesis and biological evaluation of five structurally diverse, chiral and achiral CpMn(CO) 3 (4, 7 and 8), (η 6 -arene)Cr(CO) 3 (5), and [3]ferrocenophane-1-one (6) containing platensimycin (1) derivatives are described in this report. The structures were inspired by the antibiotic platensimycin. All the chiral compounds presented in this report are racemates. The new compounds were unambiguously characterized by 1 H and 13 C NMR spectroscopy, mass spectrometry, IR spectroscopy, and elemental analysis and in certain cases by X-ray crystallography (4, 16, 18, and 29). The antibacterial and antitumor activity of selected derivatives was tested. Molecular modeling suggests that the derivatives described here may well fit into the active site of the FabF enzyme, which is the biological target of platensimycin. Hence, the antimicrobial activities of our new bioorganometallices 4−8 and the protected amide intermediates 15, 17, 18, 23, 28, 29, and 31 were tested against various Gram-positive and Gram-negative bacterial strains. However, all compounds were inactive up to concentrations of 180 μg/mL. The cytotoxicity of compounds 4 and 6 and the protected amide intermediates 15, 17,18,23,28,29, and 31 was tested against HepG2 and PT45 mammalian cancer cell lines. Surprisingly, all compounds containing a trimethylsilylethyl ester functionality at the aromatic ring (17, 23, 29, and 31) displayed rather high cytotoxicity between 2 and 9 μM.

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