title: Domino reactions for the synthesis of anthrapyran-2-ones and the total synthesis of the natural product (±)-BE-26554A.
abstract: A domino alkyne addition/CO insertion/Nu acylation reaction to a series of novel anthrapyran-2-ones in good to excellent yields is described. In addition, an efficient synthetic sequence involving carbonylation, formation of a β-keto-sulfoxide, and cyclization is presented en route to the antibiotic and antitumor compound (±)-BE-26554A.
authors.affiliation: The School of Chemistry and Biochemistry, and Centre for Microscopy, Characterisation and Analysis, The University of Western Australia , Crawley, WA 6009, Australia, and Bayer Pharma AG , Medicinal Chemistry, 42096 Wuppertal, Germany.
authors.forename: James E
authors.initials: JE
authors.lastname: Rixson
authors.forename: Brian W
authors.initials: BW
authors.lastname: Skelton
authors.forename: George A
authors.initials: GA
authors.lastname: Koutsantonis
authors.forename: Kersten M
authors.initials: KM
authors.lastname: Gericke
authors.forename: Scott G
authors.initials: SG
authors.lastname: Stewart
mesh_terms: D000215:Acylation; D000480:Alkynes / Q000737:chemistry*; D000880:Anthraquinones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D000880:Anthraquinones; D000900:Anti-Bacterial Agents; D000970:Antineoplastic Agents; C586609:BE-26554A; D001688:Biological Products