849208-87-3Relevant academic research and scientific papers
Free-radical approaches to stemoamide and analogues
Bogliotti, Nicolas,Dalko, Peter I.,Cossy, Janine
, p. 9528 - 9531 (2007/10/03)
(Chemical Equation Presented) Two approaches allowing access to the tricyclic stemona backbone are presented. Both approaches rely on a free-radical cyclization reaction as the key step. In the formal synthesis of (±)-stemoamide, the construction of the A ring of the natural product was achieved via a 5-exo-trig radical cyclization with atom transfer. The two diastereoisomers issuing from this cyclization showed different reactivity while forming the seven-membered ring of the final product. In the second part of this study, a 1-exo-trig free radical cyclization was realized allowing access to the (±)-9,10-bis-epi-stemoamide. This reaction was highly stereoselective and allowed the control of three of the four contiguous stereocenters present in the molecule.
A radical approach for the construction of the tricyclic core of stemoamide
Bogliotti, Nicolas,Dalko, Peter I.,Cossy, Janine
, p. 349 - 351 (2007/10/03)
A rapid synthesis of (±)-9,10-bis-epi-stemoamide is presented. Three of the four contiguous Stereocenters of this compound were set in a diastereoselective radical 7-exo-trig cyclization, which also allowed the construction of the tricyclic core of the mo
