A short stereoselective synthesis of the protected uracil 3 '-epi-polyoxin C

作者：Gonda Jozef^*; Martinkova Miroslava; Baur Andrea

来源：Tetrahedron: Asymmetry , 2011, 22(2): 207-214.

DOI：10.1016/j.tetasy.2011.02.004

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-alpha-D-xylo-hept-5-enfuranose 6 was employed as the key step to construct the C-5 stereocentre in 5-isothiocyanato-alpha-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.

• 出版日期2011-1-31