61(P-41) アミノ糖系抗生物質グリコシンナスペリミシンDの合成研究(ポスター発表の部)

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In 1985, Umezawa et al. reported the isolation of a novel antibiotic, glycocinnasperimicin D, from the fermentation broth of Nocardia strain. Its structure was elucidated by spectroscopic studies, which clarified that this amino sugar antibiotic belongs to a member of glycocinnamoylspermidine. Glycocinnasperimicin D has demonstrated broad antibacterial spectrum and several unique structural features; the left position is 2-ureid-pentose and the right part is 2,4-diamino-2,4,6-trideoxy-α-D-glucopylanose with p-cinnamoyl spermidine aglycon. These two amino sugars are jointed with urea glycosyl linkage. The interesting structure and small availability of glycocinnasperimicin D from natural sources promoted us to pursue the synthetic work. Retrosynthetically, glycocinnasperimicin D is divided into the amino sugar A and amino sugar B. A key steps in the synthetic scheme with amino sugar A is Soai asymmetric alkylation and a sigmatropic rearrangement of an allyl cyanate to give allyl amine stereoserectively. Further transformation into hexopyranose structure by oxydative olefin cleavage, and introduction of isonitrile at the anomeric position afford amino sugar B in 21 steps starting from D-tartaric acid. In the synthesis of amino sugar A, an iodination of phenylglycoside and the Heck reaction of iodo phenylglycoside with acryl spermidineamide furnished the cinnamoyl glycoside in good yield. Further azide introduction at C-4 position afford amino sugar A in 16 steps starting from tri-o-acetyl-D-galactal. Glycosyl isocyanate generated from glycosyl isonitrile of amino sugar B reacted with amine derived from amino sugar A to result in the construction of urea glycoside. Further introduction of urea function at C-2 position of amino sugar B, and final deprotection of fully protected glycocinnasperimicin D established the first total synthesis of glycocinnasperimicin D.
天然有機化合物討論会の論文
2004-10-01

61(P-41) アミノ糖系抗生物質グリコシンナスペリミシンDの合成研究(ポスター発表の部)

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