title: Total synthesis and stereochemical reassignment of (±)-indoxamycin B.
abstract: Revised version: the first total synthesis of indoxamycin B leads to a stereochemical reassignment of the natural product. The synthetic route features an efficient carboannulation sequence to rapidly access the dihydroindenone system. Moreover, a series of Au(I)-catalyzed transformations served in the construction of the sterically congested core framework.
authors.affiliation: Laboratorium für Organische Chemie, ETH Zürich, Switzerland.
authors.forename: Oliver F
authors.initials: OF
authors.lastname: Jeker
authors.forename: Erick M
authors.initials: EM
authors.lastname: Carreira
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity; D002384:Catalysis; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D003500:Cyclization; D006046:Gold / Q000737:chemistry; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity; D006801:Humans; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D011422:Propionates / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity; D013237:Stereoisomerism
chemical_list: D000970:Antineoplastic Agents; D006575:Heterocyclic Compounds, 3-Ring; C545165:Indoxamycin B; D011422:Propionates; D006046:Gold