Journal
ORGANIC LETTERS
Volume 16, Issue 4, Pages 1064-1067Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol403598k
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Funding
- University of Nottingham
- EPSRC [EP/K038869/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/K038869/1] Funding Source: researchfish
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The total synthesis of distomadines A and B, two structurally unique tetracyclic quinolines, is described. The route features a three-step process to access the pyranoquinoline butenolide rings via a Suzuki cross coupling of a 5-bromo-4-methoxycarbonylmethoxyquinoline with a vinyl boronate, followed by an alpha-ketohydroxylation and double cyclization by intramolecular aldol condensation and lactonization. Subsequent manipulation of the side chain to introduce the guanidine fragment completed the synthesis of distomadine B, whereas the distomadine A congener resulted from decarboxylation of a late-stage intermediate.
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