Journal
SYNLETT
Volume -, Issue 8, Pages 1277-1280Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0028-1088132
Keywords
diazonium salts; Heck reaction; cyclization; butenolides; rubrolides
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Funding
- GlaxoSmithKline
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The palladium-catalyzed reaction of arenediazonium tetrafluoroborates with methyl 4-hydroxy-2-butenoate in MeOH under mild conditions gives 4-arylbutenolides usually in good to high yields through a domino vinylic substitution/cyclization process. The reaction tolerates a variety of useful substituents including the whole range of halogen substituents, nitro, ether, cyano, keto, and ester groups and can be performed as a one-pot process generating the arenediazonium salt in situ. By using this method, the marine antibiotic rubrolide E has been synthesized via an expeditious and efficient sequential protocol that omits the isolation of the butenolide intermediate (two operative steps, 52% overall yield).
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