Isocyanoacetate Derivatives: Synthesis, Reactivity, and Application

被引:521
作者
Gulevich, Anton V. [1 ]
Zhdanko, Alexander G. [1 ]
Orru, Romano V. A. [2 ]
Nenajdenko, Valentine G. [1 ]
机构
[1] Moscow MV Lomonosov State Univ, Dept Chem, Moscow 119991, Russia
[2] Vrije Univ Amsterdam, Dept Chem & Pharmaceut Sci, NL-1081 HV Amsterdam, Netherlands
基金
俄罗斯基础研究基金会;
关键词
ALPHA-METALATED ISOCYANIDES; ASYMMETRIC ALDOL REACTION; AMINO-ACID DERIVATIVES; SOLID-PHASE SYNTHESIS; CHIRAL FERROCENYLAMINE LIGANDS; PINCER PALLADIUM COMPLEXES; FREE-RADICAL CYCLIZATION; ONE-STEP SYNTHESIS; REACTION/RING-CLOSING METATHESIS; SHORT STEREOSELECTIVE-SYNTHESIS;
D O I
10.1021/cr900411f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The sphingolipid bases, D-erythro- and D-threo-sphingosines, are the target molecules that have been synthesized to demonstrate the efficiency of a new methodology to control both absolute and relative configurations in acyclic systems. Tubulysins are compounds of extraordinary potency, rapidly degrading the tubulin cytoskeleton, with tubulysin D being the most active tubulin-modifier known so far. Among other isonitriles, isocyanoacetate derivatives occupy an important place in the field of synthetic application and reaction diversity, which makes them strongly attractive objects for investigation. The unique multifunctional nature of isocyanoacetic acid derivatives opens up a range of exciting reactions, especially tandem/cascade processes for the synthesis of complex cyclic and macrocyclic systems. Multicomponent chemistry of isocyanoacetates is also a powerful instrument to access different classes of biochemically relevant compounds such as peptides, peptide molecules, and nitrogen heterocycles.
引用
收藏
页码:5235 / 5331
页数:97
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