30 Streptolidineの合成研究

概要

論文の詳細を見る
Streptolidine (roseonine, geamine) is a component amino acid of a number of antibiotics of Streptothricin group. The structure of this guanidino amino acid was determined recently by X-ray analysis. We attempted, in this report, to synthesize it through stereospecific route starting from D-ribose. Most promising synthetic scheme was involved in guanidino ring formation from 2,3,5-triamino-4-hydroxy pentanoic acid lactam which was obtained by oxydation of 2,3,5-tribenzamido-2,3,5-trideoxy-D-arabinofuranose prepared from D-ribose through several synthetic steps. Thus, D-ribose could be converted to methyl 5-benzamido-2,3-benzoylepimino-2,3,5-trideoxy-β-D-lyxofuranoside by tosylation followed by action of sodium azide. The epimino ring in this compound was opened to 3-azido-2-benzamido derivative which was then changed to tribenzamido compound mentioned above. Reaction of crude 2,3,5-triamino-4-hydroxy pentanoic acid lactam with cyanogen bromide gave a spot of streptolidine on paperelectrophoresis, although the final step of this synthesis requires a prudent reinvestigation.
天然有機化合物討論会の論文
1973-10-01