Add time:07/28/2019         Source:sciencedirect.com

The first total synthesis of 6,17-dihydroxy-1,6,12,17-tetraazacyclodocosane-2,5,13,16-tetrone (bisucaberin) is presented. The synthetic scheme employed in this study illustrates the utility of O-benzyl-N-(tert-butoxycarbonyl)-N-(4-cyanobutyl)hydroxylamine 3, as an intermediate in the synthesis of both bisucaberin and desferrioxamine B. The bisucaberin macrocyclic lactam precursor, a linear ω-amino acid 10, is constructed from the intermediates 3 and O-benzyl-N-(4-cyanobutyl)hydroxylamine 4, utilizing a series of sequential acylations and nitrile reductions. Cyclization of 10 generates the 22 membered ring, 6,17-dibenzylbisucaberin 11. Deprotection of the hydroxamates in the last step affords the natural product, bisucaberin 1.

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