Intramolecular Diels-Alder reaction of dinitro-olefin derivatives of furan for the preparation of a versatile tool: 3,7-Dinitro-11- oxatricycloundec-9-ene

Article abstract of DOI:10.1016/S0040-4020(97)10411-2

Recurrent additions of nitromethane on furfuraldehyde followed by an intramolecular DielsAlder reaction allowed the obtention of the title compound 1 in good yield with excellent stereoselectivity. Aromatization, ether cleavage and stereocontrolled oxidation reactions give evidence of the synthetic versatility of this adduct in the preparation of ergot alkaloids and valienamine bicyclic.