Total synthesis of ageladine A, an angiogenesis inhibitor from the marine sponge Agelas nakamurai.
[reaction: see text] A 12-step total synthesis of the tricyclic heteroaromatic marine metabolite ageladine A has been achieved using a 6pi-azaelectrocyclization and a Suzuki-Miyaura coupling of N-Boc-pyrrole-2-boronic acid with a chloropyridine as key steps.
Meketa
Matthew L
ML
Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, USA.
Weinreb
Steven M
SM
D047230:Agelas / Q000737:chemistry; D020533:Angiogenesis Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000818:Animals; D002384:Catalysis; D006842:Hydrocarbons, Brominated / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D008386:Marine Biology; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
C482289:Ageladine A; D020533:Angiogenesis Inhibitors; D006842:Hydrocarbons, Brominated; D011758:Pyrroles