Stereocontrolled synthesis of retinoids functionalized at C-13 by Suzuki coupling reactions

被引：14

作者：

Alvarez, R ^{[1
]}

Iglesias, B ^{[1
]}

de Lera, AR ^{[1
]}

机构：

[1] Univ Vigo, Dept Quim Fis & Quim Organ, Vigo 36200, Spain

来源：

TETRAHEDRON | 1999年 / 55卷 / 48期

关键词：

retinoids; Suzuki reactions; stereocontrol; polyenes;

D O I：

10.1016/S0040-4020(99)00861-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The retinal analogues (13Z)-13-bromo-13-desmethylretinal (3) and (13E)-20,20,20-trifluororetinal (4) have been efficiently synthesized using the palladium-catalyzed cross-coupling of boronic acid 8 and electrophiles 9 and 10, respectively. For the first analogue, the coupling of 8 and the gem-dibromide 9 took place with high stereoselectivity. The configuration of the C13-C14 double bond in 4 relied on the stereoselective preparation and coupling of alkenyltriflate Z-10 from beta-ketoester 15. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：13779 / 13790

页数：12

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