Cytotoxic alkaloids motuporamines A-C: synthesis and structural verification

formula: see text] The unusual structure and biological properties of the marine alkaloids motuporamines A-C, as well as the uncertainty as to the position of the olefin within the ring of motuporamine C, led us to synthesize these compounds. The strategy utilized the ring-closing metathesis reaction to form the 14- and 15-membered rings and Michael addition and amidation chemistry to introduce the spermine-like unit. The syntheses, structure assignment verifications, and also the determination of the position of the olefin in motuporamine C are described.