Synthesis of Gentamine C1a from Neamine Using Ionic Displacement and Radical Elimination Methods |
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| Authors: | Derek H R Barton Duo-Kai Zheng Stephan D Géro |
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| Institution: | Institut de Chimie des Substances Naturelles, C.N.R.S. , 91190, Gif-sur-Yvette, France |
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| Abstract: | Abstract The conversion of tetra-N-benzyloxycarbonyl-5,6-O-cyclohexylidene neamine (8) into the corresponding olefin 13 has been investigated by three methods. Application of the Tipson-Cohen procedure via the dimesylate 10 gave a low yield (22%), as did the reaction of the diol 8 with triphenylphosphine-iodine-imidazole reagent (42%). Contrastingly, reductive radical elimination via the dixanthate 11 gave a synthetically useful yield (64%) without any chromatographic purification. |
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