444586-12-3Relevant academic research and scientific papers
Enantioselective synthesis of 12-amino alkylidenecyclopentenone prostaglandins
Roulland, Emmanuel,Monneret, Claude,Florent, Jean-Claude,Bennejean, Caroline,Renard, Pierre,Leonce, Stephane
, p. 4399 - 4406 (2002)
An enantioselective synthesis of new 12-amino alkylidenecyclopentenone prostaglandins is reported. The key step of the synthesis involved a [3.3] sigmatropic rearrangement of an asymmetric allylic cyanate to elaborate an asymmetric 5-amino-1,6-diene which was further transformed into cyclopentenone by successive ring-closing metathesis reaction catalyzed by the Grubbs reagent and one-pot oxidation. A palladium-catalyzed cross-coupling reaction on a 5-iodo-1,5-diene allowed the synthesis of prostanoids with variable Rw side chains. These new compounds exhibit high cytotoxic activities.
