A short stereoselective synthesis of the protected uracil 3′-epi-polyoxin C |
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Authors: | Jozef Gonda Miroslava MartinkováAndrea Baur |
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Institution: | Institute of Chemical Sciences, Department of Organic Chemistry, P.J. Šafárik University, Moyzesova 11, Sk-040 01 Košice, Slovak Republic |
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Abstract: | A short synthetic approach to the protected uracil 3′-epi-polyoxin C 20 has been developed. The stereoselective 3,3]-sigmatropic rearrangement of the corresponding 7-thiocyanato-α-d-xylo-hept-5-enfuranose 6 was employed as the key step to construct the C-5 stereocentre in 5-isothiocyanato-α-d-gluco-hept-6-enfuranose 8 and the formal synthesis of uracil 3′-epi-polyoxin C has been accomplished for the first time. This synthesis provides a facile method for multigram scale preparation and thus is useful for the research into the polyoxins’ structure-activity relationship and to search for more potent and effective anticandidal agents. |
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