title: Stereoselective total synthesis and structural elucidation of (-)-indoxamycins A-F.
abstract: In this study, a concise and stereoselective approach for the divergent total synthesis of (-)-indoxamycins A-F is described. The key steps of the strategy include an Ireland-Claisen rearrangement, an enantioselective 1,6-enyne reductive cyclization, and a tandem 1,2-addition/oxa-Michael/methylenation reaction. The relative and absolute configuration of these natural products has been unambiguously elucidated, and their cytotoxic activities against HT-29 and A-549 tumor cell lines are also reported.
authors.affiliation: Department of Chemistry, Zhejiang University, 148 Tianmushan Road, Hangzhou 310028 (China).
authors.forename: Chi
authors.initials: C
authors.lastname: He
authors.forename: Chenlong
authors.initials: C
authors.lastname: Zhu
authors.forename: Bingnan
authors.initials: B
authors.lastname: Wang
authors.forename: Hanfeng
authors.initials: H
authors.lastname: Ding
mesh_terms: D039903:Actinobacteria / Q000737:chemistry; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001688:Biological Products / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D045744:Cell Line, Tumor; D003500:Cyclization; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D008958:Models, Molecular; D009369:Neoplasms / Q000188:drug therapy; D011422:Propionates / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism
chemical_list: D000970:Antineoplastic Agents; D001688:Biological Products; D006575:Heterocyclic Compounds, 3-Ring; C545164:Indoxamycin A; C545165:Indoxamycin B; C545167:Indoxamycin C; C545168:Indoxamycin D; D011422:Propionates; C000589412:indoxamycin F
keywords: biological evaluation; enyne cyclization; structure elucidation; tandem reaction; total synthesis