Sarabia Francisco, Martín-Ortiz Laura, López-Herrera F Jorge
Departamento de Bioquímica, Biología Molecular y Química Orgánica, Facultad de Ciencias, Universidad de Málaga, 29071-Málaga, Spain.
Org Lett. 2003 Oct 16;5(21):3927-30. doi: 10.1021/ol0355074.
[reaction: see text] A synthetic approach toward the liposidomycins, a family of complex nucleoside-type antibiotics, is reported based on the synthesis of epoxy-amides derived from the reaction of sulfur ylides with the uridyl aldehyde derivative 6. To this end, the epoxy-amide derivative of indoline 14 was stereoselectively prepared and, after treatment with DDQ, transformed into the corresponding N-indole epoxyamide 15. The indole 15 provides ready access to a variety of structures related to the diazepanone core present in the liposidomycins by reaction with a variety of amines.
[反应：见正文] 报道了一种合成脂霉素（一类复杂的核苷型抗生素）的方法，该方法基于硫叶立德与尿苷醛衍生物6反应生成的环氧酰胺的合成。为此，立体选择性地制备了吲哚啉14的环氧酰胺衍生物，并在经2,3-二氯-5,6-二氰基-1,4-苯醌（DDQ）处理后转化为相应的N-吲哚环氧酰胺15。吲哚15通过与多种胺反应可方便地得到与脂霉素中存在的二氮杂环庚酮核心相关的多种结构。
