Diels-Alder cycloaddition of o-quinonedimethides and alkylidene-5H-furan-2-ones: new and rapid access to lambertellol cores and arthrinone derivatives

被引：18
作者：
Blanc, Romain [1 ]
Heran, Virginie [1 ]
Rahmani, Raphael [1 ]
Commeiras, Laurent [1 ]
Parrain, Jean-Luc [1 ]
机构：
[1] Aix Marseille Univ, Inst Sci Mol Marseille, UMR 6263, Ctr St Jerome,CNRS,Serv 532, F-13397 Marseille 20, France
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2010年 / 8卷 / 24期
关键词：
FISCHER CARBENE COMPLEXES; GAMMA-ALKYLIDENEBUTENOLIDES; BIRADICAL MECHANISM; SITE SELECTIVITY; 5-METHYLENE-2(5H)-FURANONES; QUINODIMETHANES; PROTOANEMONIN; DIENOPHILES; BUTADIENE; DIENES;
D O I：
10.1039/c0ob00448k
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient synthesis of deoxy-lambertellols was reported through a highly chemo-and diastereoselective intermolecular Diels-Alder cycloaddition between trans-1,2-disiloxybenzocyclobutenes and 2-methylprotoanemonine. Such transformation with delta-substituted gamma-alkylidenebutenolides, to prepare new analogues of these tricyclic spirolactones, which would be very difficult to prepare by other ways, was also studied.
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页码：5490 / 5494
页数：5
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