Total synthesis of enhygrolide A and analogs

被引:4
作者
Sghairi, Douha [1 ,2 ]
Romdhani-Younes, Moufida [2 ]
Guilloteau, Vincent [1 ]
Petrignet, Julien [1 ]
Thibonnet, Jerome [1 ]
机构
[1] Univ Tours, Fac Sci & Tech, Lab Synthese & Isolement Mol BioActives SIMBA, EA 7502, Parc Grandmt, F-37200 Tours, France
[2] Univ Tunis ElManar, Fac Sci Tunis, Dept Chim, Lab Chim Bio Organ Struct & Polymeres LR99ES14, Campus Univ, El Manar 2092, Tunisia
关键词
Alkylidene butenolides; Natural product; Cross-coupling; Total synthesis; GAMMA-ALKYLIDENEBUTENOLIDES; ISOCOUMARINS; METABOLITES; ACCESS;
D O I
10.1016/j.tetlet.2020.151786
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The total synthesis of enhygrolide A, a gamma-alkylidene butenolide natural product which exhibits antibacterial activities, is reported. The synthetic route features several key transformations, including a copper mediated Sonogashira/oxacyclization 5-exo-dig process to generate the alkylidene butenolide system and a Suzuki cross-coupling to introduce the benzylic unit. The methodology employed for this total synthesis represents a sufficiently flexible route to allow the synthesis of numerous analogs of these enhygrolides. (C) 2020 Elsevier Ltd. All rights reserved.
引用
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页数:4
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