Towards synthesis of kavalactone derivatives

被引：29
作者：
Amaral, Patricia A. [1 ,2 ]
Gouault, Nicolas [1 ]
Le Roch, Myriam [1 ]
Eifler-Lima, Vera L. [2 ]
David, Michele [1 ]
机构：
[1] Univ Rennes 1, Univ Europeenne Bretagne, EA Substances Lichen & Photoprotect 4090, F-35043 Rennes, France
[2] Univ Fed Rio Grande do Sul, Lab Sintese Organ Med, Porto Alegre, RS, Brazil
来源：
TETRAHEDRON LETTERS | 2008年 / 49卷 / 47期
关键词：
Kavalactones; Heck reaction; Suzuki-Miyaura reaction; Yangonin;
D O I：
10.1016/j.tetlet.2008.07.102
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Kavalactone derivatives were synthesized using a Heck reaction of the 4-methoxy-6-vinyl-5,6-dihydropyran-2-one with aryl iodides. The Suzuki-Miyaura reaction of an aryl boronic acid and (Z)-4-methoxy-6-(2-iodovinyl)-5,6-dihydropyran-2-one has also been successfully used to produce both Z and E isomers of lactones. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码：6607 / 6609
页数：3
相关论文
共 40 条
[1]   Stereoselective syntheses of naturally occurring 5,6-dihydropyran-2-ones [J].
Alberto Marco, J. ;
Carda, Miguel ;
Murga, Juan ;
Falomir, Eva .
TETRAHEDRON, 2007, 63 (14) :2929-2958
[2]  
Amaral PD, 2005, J PHARM PHARM SCI, V8, P69
[3]   EXTRACT OF KAVA (PIPER-METHYSTICUM) AND ITS METHYSTICIN CONSTITUENTS PROTECT BRAIN-TISSUE AGAINST ISCHEMIC DAMAGE IN RODENTS [J].
BACKHAUSS, C ;
KRIEGLSTEIN, J .
EUROPEAN JOURNAL OF PHARMACOLOGY, 1992, 215 (2-3) :265-269
[4]   Catalysts for Suzuki-Miyaura coupling processes: Scope and studies of the effect of ligand structure [J].
Barder, TE ;
Walker, SD ;
Martinelli, JR ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (13) :4685-4696
[5]   The heck reaction as a sharpening stone of palladium catalysis [J].
Beletskaya, IP ;
Cheprakov, AV .
CHEMICAL REVIEWS, 2000, 100 (08) :3009-3066
[6]   Kava-kava and anxiety: Growing knowledge about the efficacy and safety [J].
Bilia, AR ;
Gallon, S ;
Vincieri, FF .
LIFE SCIENCES, 2002, 70 (22) :2581-2597
[7]   Synthetic approaches to α,β-unsaturated δ-lactones and lactols [J].
Boucard, Valerie ;
Broustal, Garance ;
Campagne, Jean Marc .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (02) :225-236
[8]   THE TOTAL SYNTHESIS OF (+/) KAWAIN VIA A HETERO-DIELS-ALDER CYCLOADDITION [J].
CASTELLINO, S ;
SIMS, JJ .
TETRAHEDRON LETTERS, 1984, 25 (37) :4059-4062
[9]  
Dharmaratne HRW, 2002, PHYTOCHEMISTRY, V59, P429
[10]   Enantioselective catalysis of the hetero-Diels-Alder reaction between Brassard's diene and aldehydes by hydrogen-bonding activation:: A one-step synthesis of (S)-(+)-Dihydrokawain [J].
Du, HF ;
Zhao, DB ;
Ding, KL .
CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (23) :5964-5970
1234