title: Synthesis of the Reported Pyranonaphthoquinone Structure of the Indoleamine-2,3-dioxygenase Inhibitor Annulin B by Regioselective Diels-Alder Reaction.
abstract: Annulin B, isolated from the marine hydroid isolated from Garveia annulata, is a potent inhibitor of the tryptophan catabolizing enzyme indoleamine-2,3-dioxygenase (IDO). A synthesis of the reported pyranonaphthoquinone structure is described, in which the key step is a regioselective Diels-Alder reaction between a pyranobenzoquinone dienophile and a silyl ketene acetal diene.
authors: School of Chemistry, University of Nottingham , University Park, Nottingham NG7 2RD, U.K.
authors: Martyn
authors: M
authors: Inman
authors: School of Chemistry, University of Nottingham , University Park, Nottingham NG7 2RD, U.K.
authors: Catarina
authors: C
authors: Carvalho
authors: School of Chemistry, University of Nottingham , University Park, Nottingham NG7 2RD, U.K.
authors: William
authors: W
authors: Lewis
authors: School of Chemistry, University of Nottingham , University Park, Nottingham NG7 2RD, U.K.
authors: Christopher J
authors: CJ
authors: Moody
mesh_terms: D061565:Cycloaddition Reaction; D004791:Enzyme Inhibitors / Q000494:pharmacology*; D050503:Indoleamine-Pyrrole 2,3,-Dioxygenase / Q000037:antagonists & inhibitors*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009285:Naphthoquinones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D011714:Pyrans / Q000737:chemistry*; D011753:Pyrones / Q000737:chemistry* / Q000494:pharmacology
chemical_list: D004791:Enzyme Inhibitors; D050503:Indoleamine-Pyrrole 2,3,-Dioxygenase; D009285:Naphthoquinones; D011714:Pyrans; D011753:Pyrones; C529393:annulin B