Polyalkoxybenzenes from plant sources 2. Synthesis of isoxazoline analogs of combretastatin from natural allyl(methylenedioxy)methoxybenzenes |
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Authors: | D V Tsyganov A P Yakubov L D Konyushkin S I Firgang V V Semenov |
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Institution: | (1) N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation |
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Abstract: | A series of analogs of the natural mitostatic agent combretastatin were synthesized by the reaction of nitrile oxides with
natural allylbenzenes, such as myristicin, apiol, and dillapiol. The 1,3-dipolar cycloaddition reactions in allylic systems
proceed regiospecifically. The reactions with trans isomers of propenylbenzenes, viz., isomyristicin, isoapiol, and isodillapiol, as dipolarophiles produce regioisomers.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2375–2380, December, 2007. |
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Keywords: | isoxazolines nitrile oxides 1 3-dipolar cycloaddition myristicin apiol dillapiol |
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