Palladium-Catalyzed Reaction of Arenediazonium Tetrafluoroborates with Methyl 4-Hydroxy-2-butenoate: An Approach to 4-Aryl Butenolides and an Expeditious Synthesis of Rubrolide E

被引:44
作者
Cacchi, Sandro [1 ]
Fabrizi, Giancarlo [1 ]
Goggiamani, Antonella [1 ]
Sferrazza, Alessio [1 ]
机构
[1] Univ Roma La Sapienza, Dipartimento Chim & Tecnol Farmaco, I-00185 Rome, Italy
关键词
diazonium salts; Heck reaction; cyclization; butenolides; rubrolides; CROSS-COUPLING REACTIONS; ARYL DIAZONIUM IONS; HECK-TYPE ARYLATION; STEREOSELECTIVE-SYNTHESIS; ARYLDIAZONIUM SALTS; EFFICIENT SYNTHESIS; FACILE SYNTHESIS; DERIVATIVES; HYDROARYLATION; METABOLITES;
D O I
10.1055/s-0028-1088132
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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).
引用
收藏
页码:1277 / 1280
页数:4
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