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

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

Source and publish data:

Tetrahedron p. 1773 - 1782 (1998)

Update date:2022-07-29

Topics:

Authors:

Sader-Bakaouni, Lina

Charton, Olivier

Kunesch, Nicole

Tillequin, Francois

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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.

Full text of DOI:10.1016/S0040-4020(97)10411-2

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