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

Authors
Macdonald, SJF Mills, K Spooner, JE Upton, RJ Dowle, MD
Citation
Sjf. Macdonald et al., 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, J CHEM S P1, (23), 1998, pp. 3931-3936
Citations number
37
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
ISSN journal
0300922X → ACNP
Issue
23
Year of publication
1998
Pages
3931 - 3936
Database
ISI
SICI code
0300-922X(199812):23<3931:ASSVA5>2.0.ZU;2-9
Abstract
trans-2-Oxohexahydro-2H-furo[3,2-b]pyrroles (such as 2) are conformationall y strained 5,5-fused ring systems and are potent human neutrophil elastase (HNE) inhibitors. A stereoselective synthesis is described based on intramo lecular 5-exo-trig cyclisations of aldehyde acrylates 4 and 5 mediated by s amarium(II) iodide to give predominantly trans-products 9 and 15. The n-pro pyl group in 15 is also generated with stereoselectivity for the desired be ta-isomer.