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

作者：Peralta Hernandez Eduardo; Cortezano Arellano Omar; Cordero Vargas Alejandro^*

来源：Tetrahedron Letters, 2011, 52(51): 6899-6902.

DOI：10.1016/j.tetlet.2011.10.042

• Free radical
• Atom transfer reaction
• Epoxides
• Polyhydroxylated alkaloids

An efficient one-pot sequence for the preparation of epoxides from alpha-iodoesters or alpha-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.

• 出版日期2011-12-21