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

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• 作者：Eduardo Peralta-Herná ; ndez ; Omar Cortezano-Arellano ; Alejandro Cordero-Vargas  ; ;   ; ^{acordero@unam.mx}
• 关键词：Free radical ; Atom transfer reaction ; Epoxides ; Polyhydroxylated alkaloids
• 刊名：Tetrahedron Letters
• 出版年：2011
• 出版时间：21 December 2011
• 年：2011
• 卷：52
• 期：51
• 页码：6899-6902
• 全文大小：1557 K

文摘

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