Synfacts 2006(5): 0429-0429  
DOI: 10.1055/s-2006-934372
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Stereoselective Synthesis of Bicyclic Lactones from Furans

Contributor(s): Victor Snieckus, Bärbel Wittel
N. Maulide, I. E. Markó*
Université Catholique de Louvain, Belgium
Weitere Informationen

Publikationsverlauf

Publikationsdatum:
21. April 2006 (online)

Significance

Functionalized ortho-esters undergo condensation with trimethylsiloxyfuran derivatives under sub-stoichiometric Lewis acid conditions to give butenolides which, using tris(trimethylsilyl)silane (TTMSS), a ‘green’ version of the corresponding tin hydride, participate in radical-induced ring closure to afford bicyclo[3.n.0]lactones. The two-step sequence is not limited to ­dioxolane-containing ortho-esters as trialkoxy ortho-esters also participate to give products in good to high yields. In the second step, up to three contiguous stereocenters with high diaste­reoselectivity (>95%) are formed.