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Title: Synthesis of (-)-sedinine by allene cyclization and iminium ion chemistry. Author: Bates RW, Lu Y. Journal: Org Lett; 2010 Sep 03; 12(17):3938-41. PubMed ID: 20704308. Abstract: A synthesis of the sedum alkaloid sedinine has been achieved employing silver(I)-catalyzed allenic hydroxylamine cyclization and ring-closing metathesis to form a bicyclic N,O-acetal. Ring opening of this acetal with a silyl enol ether under Lewis acidic conditions is exclusively trans selective, leading to the natural product after reduction. On the other hand, conversion of the bicyclic N,O-acetal to a semicyclic N,O-acetal results in no stereoselectivity during such a reaction. The contrasting results can be rationalized by consideration of the conformation of the iminium ions.[Abstract] [Full Text] [Related] [New Search]