A practical one-pot radical-ionic sequence for the preparation of epoxides: application to the synthesis of unnatural polyhydroxylated alkaloids

An efficient one-pot sequence for the preparation of epoxides from α-iodoesters or α-iodonitriles and allylic alcohols is described. This sequence is based on the use of iodine atom transfer reaction onto allylic alcohols followed by a ring closing epoxidation reaction of the halohydrin intermediates. The feasibility of this sequence is showcased in the synthesis of the perhydroaza-azulene, an unnatural analog of castanospermine.

Graphical abstractAn efficient sequence for the preparation of epoxides from α-iodoesters or α-iodonitriles and allylic alcohols is described. The efficiency of this sequence is showcased in the synthesis of polyhydroxylated alkaloids perhydroaza-azulenes.Figure optionsDownload full-size imageDownload as PowerPoint slide