The efficient synthesis of the common C1-C32 precursor of trans and cis solamins has been achieved with the longest linear sequence of 7 steps from pentadecalactone. The key transformations rely on the iron (III) catalysed Grignard coupling reaction with a vinyl bromide, and the Sharpless asymmetric dihydroxylation. Mitochondrial complex I activity of these annonaceous synthetic precursors highlighted the crucial influence of the terminal butenolide, as well as the tetrahydrofuanic pattern.
Keywords: acetogenins, annonaceae, synthesis, grignard, asymmetric dihydroxylation
Rights & PermissionsPrintExport