title: Total synthesis of exiguamines A and B inspired by catecholamine chemistry.
abstract: The evolution of a total synthesis of the exiguamines, two structurally unusual natural products that are highly active inhibitors of indolamine-2,3-dioxygenase (IDO), is described. The ultimately successful strategy involves advanced cross-coupling methodology and features a potentially biosynthetic tautomerization/electrocyclization cascade reaction that forms two heterocycles and installs a quaternary ammonium ion in a single synthetic operation.
authors.affiliation: Department of Chemistry, Ludwig-Maximilians-Universität Munich, Butenandtstrasse 5-13, Haus F, 81377 Munich, Germany.
authors.forename: Vladimir
authors.initials: V
authors.lastname: Sofiyev
authors.forename: Jean-Philip
authors.initials: JP
authors.lastname: Lumb
authors.forename: Matthew
authors.initials: M
authors.lastname: Volgraf
authors.forename: Dirk
authors.initials: D
authors.lastname: Trauner
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D002395:Catecholamines / Q000737:chemistry*; D003500:Cyclization; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry*; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D050503:Indoleamine-Pyrrole 2,3,-Dioxygenase / Q000037:antagonists & inhibitors* / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D011809:Quinones / Q000138:chemical synthesis* / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D002395:Catecholamines; D004791:Enzyme Inhibitors; D026121:Indole Alkaloids; D050503:Indoleamine-Pyrrole 2,3,-Dioxygenase; D007211:Indoles; D011809:Quinones; D013141:Spiro Compounds; C516830:exiguamine A; C531460:exiguamine B