Towards the rubromycins: An efficient synthesis of a suitable isocoumarin precursor, its lactam analogue, and palladium-catalyzed couplings

被引:27
作者
Brasholz, M [1 ]
Luan, XS [1 ]
Reissig, HU [1 ]
机构
[1] Free Univ Berlin, Inst Chem & Biochem, D-14195 Berlin, Germany
来源
SYNTHESIS-STUTTGART | 2005年 / 20期
关键词
isocoumarins; rubromycins; ortho-lithiation; Horner-Wadsworth-Emmons reaction; palladium catalysis;
D O I
10.1055/s-2005-918417
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
6-Iodoisocoumarin 4 and its aza-analogue, 6-iodo-I-oxo-isoquinoline 29, were efficiently prepared from vanillin in seven and six steps, respectively. Key transformations in their syntheses were achieved by directed ortho-lithiation and variations of Horner-Wadsworth-Emmons reactions. Both 6-Iodoisocoumarin 4 and its aza-analogue were designed for insertion into syntheses of rubromycin type target structures via palladium-catalyzed coupling reactions. For the isocoumarin subunit, this plan could be confirmed through Heck, Sonogashira, and Suzuki reactions of our building block with various substrates.
引用
收藏
页码:3571 / 3580
页数:10
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