title: Total synthesis of the marine pyridoacridine alkaloid demethyldeoxyamphimedine.
abstract: A four-step total synthesis of the marine pyridoacridine alkaloid demethyldeoxyamphimedine (5) is presented. With an overall yield of 6.4%, this pentacyclic compound has been synthesized by utilizing only two commercial building blocks, ethyl nicotinate and 2-iodoaniline. The final cyclization step was achieved via a directed remote ring metalation with Knochel-Hauser base (TMPMgCl·LiCl) followed by intramolecular trapping of an ester group.
authors: Department of Pharmacy - Center for Drug Research, Ludwig-Maximilians University , Butenandtstrasse 5-13, D-81377 Munich, Germany.
authors: Benedikt
authors: B
authors: Melzer
authors: Alois
authors: A
authors: Plodek
authors: Franz
authors: F
authors: Bracher
mesh_terms: D000166:Acridines / Q000138:chemical synthesis* / Q000737:chemistry; D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000814:Aniline Compounds / Q000737:chemistry*; D003500:Cyclization; D008094:Lithium / Q000737:chemistry; D008274:Magnesium / Q000737:chemistry; D015394:Molecular Structure; D009539:Nicotinic Acids / Q000737:chemistry*; D010618:Phenanthrolines / Q000138:chemical synthesis* / Q000737:chemistry; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C552400:2-iodobenzenamine; D000166:Acridines; D000470:Alkaloids; D000814:Aniline Compounds; D009539:Nicotinic Acids; D010618:Phenanthrolines; D011083:Polycyclic Compounds; C475900:pyridoacridine; C475901:amphimedine; D008094:Lithium; D008274:Magnesium; C037328:ethylnicotinate