Palladium-catalyzed hydrodehalogenation of butenolides: An efficient and sustainable access to β-arylbutenolides

TETRAHEDRON LETTERS

卷:58

Article

Karak, Milandip^1,2  Barbosa, Luiz C. A.^1,2  Maltha, Celia R. A.²  Silva, Thiago M.¹  Boukouvalas, John^1,3,4 

[1] Univ Fed Minas Gerais, Dept Chem, Av Pres Antonio Carlos 6627,Campus Pampulha, BR-31270901 Belo Horizonte, MG, Brazil

[2] Univ Fed Vicosa, Dept Chem, Av Peter Henry Rolfs S-N,Campus Univ, BR-36570900 Vicosa, MG, Brazil

[3] Univ Laval, Dept Chem, 1045 Av Med, Quebec City, PQ G1V 0A6, Canada

[4] Univ Laval, Ctr Green Chem & Catalysis, 1045 Av Med, Quebec City, PQ G1V 0A6, Canada

关键词: Reductive dehalogenation;    Suzuki cross-coupling;    Vinylogous aldol condensation;    Rubrolides synthesis;   

DOI  :  10.1016/j.tetlet.2017.06.016

来源: Elsevier

【 摘 要 】

Several alpha-unsubstituted beta-arylbutenolides have been prepared in 69-92% yield by reductive dehalogenation of alpha-halo-beta-arylbutenolides. The latter were assembled in a single-step from alpha,beta-dihalobutenolides, which are accessible on a large-scale from biomass-derived furfural. Our dehalogenation protocol is illustrated by a new synthesis of the marine antibiotics rubrolide E and F, and 3-bromorubrolide F. (C) 2017 Elsevier Ltd. All rights reserved.

【 授权许可】

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