Cascade reactions of methyl-2-chloro-2-cyclopropylideneacetate with five- and seven-membered cyclic dienolates: A novel approach to the bicyclo[4.2.1]nonane segment of the skeleton of mediterraneols

Article abstract of DOI:10.1055/s-1996-4238

The MIMIRC (Michael-Michael-Ring Closure) reaction of methyl 2-chloro-2-cyclopropylideneacetate (5) with the cyclic dienolates 6a, 6c, and the one derived from 11-R under aprotic conditions gave the tricyclic adducts 7a, 7c, and 10-R, respectively, in moderate to good yield. Compound 10-R is conceived as a potential intermediate for the synthesis of the biologically active marine diterpenes mediterraneol 1.