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.
Goldring
W P
WP
Department of Chemistry, University of British Columbia, Vancouver, Canada. billg@chem.ubc.ca
Weiler
L
L
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure
D000470:Alkaloids; D000970:Antineoplastic Agents; C409087:motuporamine A; C409086:motuporamine B; C409085:motuporamine C