220618-79-1Relevant academic research and scientific papers
A stereoselective synthesis via a 5-exo-trig cyclisation of trans-2-oxohexahydro-2H-furo[3,2-b]pyrroles (pyrrolidine-trans-lactones) - Potent, novel elastase inhibitors
Macdonald, Simon J. F.,Mills, Keith,Spooner, Julie E.,Upton, Richard J.,Dowle, Michael D.
, p. 3931 - 3936 (1998)
trans-2-Oxohexahydro-2H-furo[3,2-b]pyrroles (such as 2) are conformationally strained 5,5-fused ring systems and are potent human neutrophil elastase (HNE) inhibitors. A stereoselective synthesis is described based on intramolecular 5-exo-trig cyclisations of aldehyde acrylates 4 and 5 mediated by samarium(II) iodide to give predominantly trans-products 9 and 15. The n-propyl group in 15 is also generated with stereoselectivity for the desired β-isomer.
