A new total synthesis of the zinc matrixmetalloproteinase inhibitor ageladine A featuring a biogenetically patterned 6pi-2-azatriene electrocyclization.
[reaction: see text] A convergent second generation total synthesis of the heterocyclic marine sponge metabolite ageladine A has been achieved by using a biomimetically inspired 6pi-2-azatriene electrocyclization as the key step for formation of the imidazolopyridine moiety.
Meketa
Matthew L
ML
Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, USA.
Weinreb
Steven M
SM
D001372:Aza Compounds / Q000737:chemistry*; D003500:Cyclization; D004583:Electrons; D006571:Heterocyclic Compounds / Q000737:chemistry*; D045726:Metalloproteases / Q000737:chemistry* / Q000378:metabolism*; D015394:Molecular Structure; D011480:Protease Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D015032:Zinc / Q000737:chemistry* / Q000378:metabolism*
C519122:6pi-2-azatriene; C482289:Ageladine A; D001372:Aza Compounds; D006571:Heterocyclic Compounds; D011480:Protease Inhibitors; D011758:Pyrroles; D045726:Metalloproteases; D015032:Zinc