title: Modular total synthesis of lamellarin D.
abstract: [Chemical reaction: see text] A modular total synthesis of lamellarin D, a marine alkaloid with potent cytotoxic as well as topoisomerase I inhibition properties, has been accomplished. A sequential and regioselective bromination/Suzuki cross-coupling procedure was applied for the introduction of aryl groups at positions 1 and 2 of scaffold 1. Microwave-assisted 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) oxidation to yield pyrroloisoquinoline 15, followed by phenol group deprotection and subsequent lactonization, gave lamellarin D (18% in eight steps from 1).
authors.affiliation: Biomedical Research Institute, Barcelona Scientific Park, University of Barcelona, 08028 Barcelona, Spain.
authors.forename: Daniel
authors.initials: D
authors.lastname: Pla
authors.forename: Antonio
authors.initials: A
authors.lastname: Marchal
authors.forename: Christian A
authors.initials: CA
authors.lastname: Olsen
authors.forename: Fernando
authors.initials: F
authors.lastname: Albericio
authors.forename: Mercedes
authors.initials: M
authors.lastname: Alvarez
mesh_terms: D000470:Alkaloids; D003374:Coumarins / Q000138:chemical synthesis* / Q000737:chemistry; D004146:Dioxanes; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D059004:Topoisomerase I Inhibitors
chemical_list: D000470:Alkaloids; D003374:Coumarins; D004146:Dioxanes; D004791:Enzyme Inhibitors; D006576:Heterocyclic Compounds, 4 or More Rings; D007202:Indicators and Reagents; D007546:Isoquinolines; D059004:Topoisomerase I Inhibitors; C455554:lamellarin D; C025223:1,4-dioxane