Modular total synthesis of lamellarin D.
[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).
Pla
Daniel
D
Biomedical Research Institute, Barcelona Scientific Park, University of Barcelona, 08028 Barcelona, Spain.
Marchal
Antonio
A
Olsen
Christian A
CA
Albericio
Fernando
F
Alvarez
Mercedes
M
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
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