Modular approach to Annonaceous acetogenins. Total synthesis of asimicin and bullatacin

Article abstract of DOI:10.1016/0040-4039(95)02018-K

Starting with a variety of non-functionalized carbon skeletons and employing various combinations of five key transformations provides an easy access to most of the naturally occurring Annonaceous acetogenins. A particular emphasis is given to the dominant structural feature that appears in more than 40% of the known acetogenins. This is a linear, ten-carbon skeleton comprising two adjacent tetrahydrofurane rings flanked with two hydroxyl groups. Efficient, flexible syntheses of asimicin and bullatacin demonstrate this approach.