Highly convergent, stereospecific synthesis of 11-cis-retinoids by metal-catalyzed cross-coupling reactions of (Z)-1-alkenylmetals

被引:24
作者
Lopez, Susana [1 ]
Montenegro, Javier [1 ]
Saa, Carlos [1 ]
机构
[1] Univ Santiago de Compostela, Fac Quim, Dept Quim Organ, Santiago De Compostela 15782, Spain
关键词
D O I
10.1021/jo701664r
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] A stereospecific synthesis of 11-cis-retinoids has as its key step the hitherto unexplored palladium-catalyzed cross-coupling of trans-trienyl electrophiles and (1Z,3E)-penta-1,3-dienyl boronates (a Suzuki-Miyaura reaction) or stannanes (a Stille reaction). This highly convergent approach constitutes the first application of cis-organometallic moieties to the synthesis of 11-cis-retinoids and represents a general, straightforward route to the visual chromophore..
引用
收藏
页码:9572 / 9581
页数:10
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