The total synthesis of the diepoxycyclohexanone antibiotic aranorosin and novel synthetic analogues
作者:Alexander McKillop、Lee McLaren、Richard J. K. Taylor、Robert J. Watson、Norman J. Lewis
DOI:10.1039/p19960001385
日期:——
A short synthesis of the novel antibiotic aranorosin in chiral form is described which employs (i) a novel hypervalent iodine-mediated oxidative hydroxylation of a tyrosinal derivative and (ii) a stereocontrolled cis-bisepoxidation in the key steps. A similar procedure was employed to prepare 6′-epiaranorosin, and hence establish the stereochemistry of the natural compound, and to prepare novel aranorosin
描述了手性形式的新型抗生素阿糖胞苷的简短合成,其在关键步骤中采用了(i)酪氨酸衍生物的新型高价碘介导的氧化羟基化作用和(ii)立体控制的顺式-双环氧化。采用相似的方法制备6'-表皮阿糖胞苷,从而建立天然化合物的立体化学,并制备新的阿糖胞苷类似物。描述了一种有机金属路线,该路线产生了脱酰胺基芳族松香。