Synthesis of Analogues of the Mutagenic Sesquiterpenes Isovelleral and Merulidial via Stereoselective Cyclopropanation of Cyclohexenecarbaldehydes

Article abstract of DOI:10.1016/0040-4020(95)00108-K

Stereoselective cyclopropanation of 5-acetoxy-6-(diethoxymethyl)-1-cyclohexenecarbaldehyde and its 2-methyl derivative with dimethyl sulfoxonium methylide yielded, after acetal hydrolysis and elimination, bicyclo<4.1.0>hept-2-ene-1,2-dicarbaldehyde and its 6-methyl derivative.The products contain the chemical functionalities that are responsible for the bioactivities of the fungal sesquiterpenes isovelleral and merulidial, and the results presented here indicate that the cyclopropane ring plays a crucial role for the mutagenic activity of these compounds in the Ames' Salmonella assay.