492-49-9Relevant academic research and scientific papers
Synthesis of (-)-sedinine by allene cyclization and iminium Ion chemistry
Bates, Roderick W.,Lu, Yongna
supporting information; experimental part, p. 3938 - 3941 (2010/11/04)
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.
Sedum alkaloids. V. Sedacrine, the major alkaloid of Sedum acre, and related bases
Colau, Brigitte,Hootele, Claude
, p. 470 - 472 (2007/10/02)
Sedacrine, the major alkaloid of Sedum acre, is assigned structure 5 on the basis of spectroscopic and chemical evidence.Two minor bases, sedinone 6 and dihydrosedinine 7, are described.Sedacrine 5, sedinone 6, dihydrosedinine 7, and sedinine 3 are correl
