L. Sonaglia, L. Banfi, R. Riva
Nov 28, 2012
Citations
0
Influential Citations
8
Citations
Journal
Tetrahedron Letters
Abstract
Abstract N -Allyl 3- endo -amino-7-oxabicyclo[2.2.1]hept-5-ene-2- exo -carboxylic acid has been synthesized and has been employed in a Ugi-5-centre-4-component reaction (U-5C-4CR) with various aldehydes and isocyanides; by employing a mixture of methanol and trifluoroethanol the reaction was completely stereoselective. The resulting products have been employed in an unprecedented ring-opening/ring-closing metathesis process with Ru catalyst, to afford stereochemically defined, polysubstituted cis -fused hexahydrofuro[3,2- b ]pyridine derivatives in moderate to good yields. This straightforward procedure allows to assemble in just two synthetic steps natural product-like compounds having the 2-aza-7-oxabicyclo[4.3.0]nonane framework, displayed by various alkaloids.