Cascade cyclization: an easy access to highly unsaturated polycyclic ring systems through a tandem stille/[4 + 2] reaction under mild conditions

Sébastien Brückner; Estelle Abraham; Philippe Klotz; Jean Suffert

doi:10.1021/ol0264253

Cascade cyclization: an easy access to highly unsaturated polycyclic ring systems through a tandem stille/[4 + 2] reaction under mild conditions

Org Lett. 2002 Oct 3;4(20):3391-3. doi: 10.1021/ol0264253.

Authors

Sébastien Brückner¹, Estelle Abraham, Philippe Klotz, Jean Suffert

Affiliation

¹ Université Louis Pasteur de Strasbourg (UMR 7081 CNRS/ULP), Faculté de Pharmacie, 74 route du Rhin, 67401 Illkirch-Cedex, France.

PMID: 12323026
DOI: 10.1021/ol0264253

Abstract

The synthesis of several polycyclic compounds 1a-c, 2, and 3 has been performed through a tandem Stille/[4 + 2] cascade reaction from cyclic bis(enoltrifluomethanesulfonate) 4a-c, 5, and 6, respectively. The reaction proceeds very efficiently in a one-pot operation at roomtemperature in DMF in the presence of a catalytic amount of Pd(CH(3)CN)(2)Cl(2) and LiCl.[reaction: see text]