University of Chicago, Department of Chemistry, 5735 South Ellis Avenue, Chicago, Illinois 60637, USA.
J Am Chem Soc. 2010 Oct 20;132(41):14394-6. doi: 10.1021/ja107190w.
Streptolydigin is a highly potent, broad-spectrum antibiotic produced by Streptomyces lydicus, which inhibits bacterial RNA polymerase. We describe the first synthesis of streptolydigin, which was assembled in a highly convergent and fully stereocontrolled fashion with a longest linear sequence of 24 steps starting from commercially available precursors. The assembly process entailed preparation of fully elaborated streptolic and ydiginic subunits of the natural product, followed by a highly efficient union in a three-step one-pot procedure, which included Dieckmann cyclization with a concomitant imide opening, Horner-Wadsworth-Emmons olefination, and desilylation.
链丝菌素是一种由链霉菌产生的高效广谱抗生素，它可以抑制细菌 RNA 聚合酶。我们首次合成了链丝菌素，它采用高度收敛和完全立体控制的方式组装而成，从商业上可获得的前体开始，最长线性序列为 24 步。组装过程包括制备天然产物的全修饰链丝菌素和酰氨霉素亚单位，然后通过三步一锅法进行高效的缩合反应，其中包括伴有酰亚胺开环的狄克曼环化、霍纳-沃兹沃思-埃蒙斯烯烃化和脱硅反应。
