通过（Z）-1-链烯基金属的金属催化交叉偶联反应高度收敛、立体专一性合成11-顺式视黄醛。

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

作者信息

López Susana, Montenegro Javier, Saá Carlos

机构信息

Departamento de Química OrgAnica, Facultade de Química, Universidade de Santiago de Compostela, 15782 Santiago de Compostela, Spain.

出版信息

J Org Chem. 2007 Dec 7;72(25):9572-81. doi: 10.1021/jo701664r. Epub 2007 Nov 15.

DOI:10.1021/jo701664r

PMID:18001096

Abstract

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.

摘要

11-顺式视黄醛类化合物的立体定向合成的关键步骤是此前未被探索的钯催化反式三烯基亲电试剂与(1Z,3E)-戊-1,3-二烯硼酸酯（铃木-宫浦反应）或锡烷（施蒂勒反应）的交叉偶联。这种高度汇聚的方法是顺式有机金属部分在11-顺式视黄醛类化合物合成中的首次应用，代表了一种通向视觉发色团的通用、直接的途径。