A Formal Intermolecular Iodolactonization Reaction Based on a Radical-Ionic Sequence

作者:Leon Rayo David F; Morales Chamorro Maricela; Cordero Vargas Alejandro
来源:European Journal of Organic Chemistry, 2016, 2016(9): 1739-1750.
DOI:10.1002/ejoc.201600051

摘要

We report herein a method based on a radical-ionic sequence between an allylic alcohol and an a-iodo acid in the presence of substoichiometric amounts of lauroyl peroxide (DLP) to produce an atom transfer radical addition (ATRA) adduct, which subseqently underwent an acid-mediated lactonization. This approach can be described as a free radical reaction followed by an intermolecular iodolactonization. Twenty-two experiments were carried out to evaluate the scope of the reaction, which afforded a wide variety of iodo lactones with diverse functionalities. The utility of this approach was demonstrated in the synthesis of the natural product (-)-de-O-methylcentrolobine.

  • 出版日期2016-3