2008
DOI: 10.1002/ejoc.200800957
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A Novel Approach to Combretastatins: From trans‐Epoxide to CA‐4 and Its Dioxolane Derivative

Abstract: The trans‐epoxide derivative of Combretastatin A‐4 wasstereoselectively prepared in good yield by sulfur ylide mediated epoxidation of silyl‐protected isovanillin. From this key intermediate, a formal synthesis of CA‐4, by stereoselective deoxygenation and photoisomerization, was achieved. Alternatively, a trans‐dioxolane derivative was obtained bystereoselective acetone insertion.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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Cited by 12 publications
(7 citation statements)
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“…It is well-documented that the ISC rate constant depends strongly on the polarity of the solvent, the rate being higher in less polar solvents. [18] Conversely, because the pericyclic reaction occurs through a singlet excited state it is more favored in polar reaction mediums, such as MeOH, [19] in which the rate of ISC is very low. Oxygen plays two essential roles: as an enone triplet quencher and an oxidant in the tandem electrocyclization/ oxidative aromatization reaction.…”
Section: Resultsmentioning
confidence: 98%
See 1 more Smart Citation
“…It is well-documented that the ISC rate constant depends strongly on the polarity of the solvent, the rate being higher in less polar solvents. [18] Conversely, because the pericyclic reaction occurs through a singlet excited state it is more favored in polar reaction mediums, such as MeOH, [19] in which the rate of ISC is very low. Oxygen plays two essential roles: as an enone triplet quencher and an oxidant in the tandem electrocyclization/ oxidative aromatization reaction.…”
Section: Resultsmentioning
confidence: 98%
“…Chromatographic purifications performed on a Combiflash (Teledyne Isco) automated chromatography system with silica gel RediHep columns. 1 H, 13 C and 19 F NMR spectra were recorded at room temperature on a Varian Mercury 400 spectrometer and were referenced to residual solvent peaks. Signal multiplicities in the 13 C NMR spectra have been assigned with the aid of DEPT and HSQC experiments.…”
Section: Methodsmentioning
confidence: 99%
“…2, 132.1, 128.1, 113.5, 78.76, 55.16. 6, 136.6, 129.4, 120.2, 114.3, 113.7, 60.5, 55.4. 8c: 2,3-bis (3,4-dimethoxyphenyl)oxirane [25], 51% yield. 1 H NMR (400 MHz, CDCl 3 )  6.67-6.63 (2H, d, J = 6.7 Hz), 6.59-6.57 (3H, d, J = 6.7 Hz), 6.57-6.56 (1H, d), 4.55 (2H, s), 3.76 (6H, s), 3.69 (6H, s).…”
Section: Synthesis and Antioxidant Activity Of Stilbene Derivativesmentioning
confidence: 99%
“…14 This last reaction was successfully applied to a calix [4]arene bis-epoxide 15 and to the synthesis of Combretastatine derivatives. 16 These results prompted us to investigate water as the nucleophile in the presence of Amberlyst 15 with a variety of 2,3-diaryloxiranes.…”
Section: Introductionmentioning
confidence: 98%