Facile synthesis of the trans-fused azabicyclo[3.3.0]octane core of the palau'amines and the tricyclic core of the axinellamines from a common intermediate.
A facile synthesis of the trans-fused azabicyclo[3.3.0]octane core of palau'amine and related pyrrole-imidazole alkaloids is described. Following gamma-lactam cleavage with concomitant epimerization at C12 of a previously reported tricycle, a facile intramolecular Mitsunobu reaction delivered the fully functionalized tricyclic core common to several members of the oroidin-derived alkaloids including palau'amine. An alternative cyclization of a related intermediate provides the tricyclic "aza-angular triquinane" core of the axinellamines.
Zancanella
Manuel A
MA
Department of Chemistry, Texas A&M University, P.O. Box 30012, College Station, Texas 77842-3012, USA.
Romo
Daniel
D
D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry; D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D006146:Guanidines / Q000138:chemical synthesis* / Q000737:chemistry; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D009795:Octanes / Q000138:chemical synthesis* / Q000737:chemistry; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D001372:Aza Compounds; D006146:Guanidines; D007093:Imidazoles; D009795:Octanes; D011758:Pyrroles; D013141:Spiro Compounds; C520388:axinellamine; C518626:azabicyclo(3.3.0)-octane; C438976:palau'amine