title: Biomimetic synthesis of the IDO inhibitors exiguamine A and B.
abstract: Biomimetic synthesis is an attempt to assemble natural products along biosynthetic lines without recourse to the full enzymatic machinery of nature. We exemplify this with a total synthesis of exiguamine A and the newly isolated natural product exiguamine B. The most noteworthy feature of this work is an oxidative endgame drawing from the complex chemistry of catecholamines, which allows for ready access to a new class of nanomolar indoleamine-2,3-dioxygenase inhibitors.
authors.affiliation: Department of Chemistry, University of California, Berkeley, California 94720, USA.
authors.forename: Matthew
authors.initials: M
authors.lastname: Volgraf
authors.forename: Jean-Philip
authors.initials: JP
authors.lastname: Lumb
authors.forename: Harry C
authors.initials: HC
authors.lastname: Brastianos
authors.forename: Gavin
authors.initials: G
authors.lastname: Carr
authors.forename: Marco K W
authors.initials: MK
authors.lastname: Chung
authors.forename: Martin
authors.initials: M
authors.lastname: Münzel
authors.forename: A Grant
authors.initials: AG
authors.lastname: Mauk
authors.forename: Raymond J
authors.initials: RJ
authors.lastname: Andersen
authors.forename: Dirk
authors.initials: D
authors.lastname: Trauner
mesh_terms: D040761:Biomimetic Materials / Q000138:chemical synthesis* / Q000737:chemistry; D002395:Catecholamines / Q000096:biosynthesis / Q000138:chemical synthesis / 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*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011809:Quinones / Q000138:chemical synthesis* / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: 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