新型大环磺酰胺肽模拟物的设计及其关键前体的合成

动植物、微生物和病毒等都含有微量的环肽 ,其中大多具有明显的生理活性 ,因此 ,受到科学家们的高度重视 1] .设计与合成具有生理活性的新型环肽是目前有机合成的前沿课题 2～ 4 ] .烯烃复分解闭环反应 ( RCM)已成为构成碳环和杂环的重要手段 5～ 7] .由于 Schrock和 Grubbs催化剂的高活性和官能基适用性 ,烯交换闭环反应已被应用于肽的合成 8～ 10 ] .在研究通过烯交换闭环反应设计与合成新型肽化合物的基础上 11] ,我们设计了通过烯交换闭环反应从含有两个末端烯双键化合物合成新型大环磺酰胺肽模拟物的新途径 ,如 Scheme 1 ,其中…

Design of a Novel Macrocyclic Sulfonamide Peptidomimetics and Synthesis of the Precursors

A route of synthesis of a novel macrocyclic sulfonamide peptidomimetics \%via\% ring closing metathesis(RCM) has been designed. Allyl glutaric anhydride has been synthesized from commercially available diethyl allylmanolate and \%tert\% butyl acrylate by the Michael reaction and hydrolysis followed by decarboxylation and dehydration. Then, allyl hydrogen 2\|allylglutarate, a precursor for RCM, has been prepared. The synthesis of N \|allyl\|2\|ethoxycarbonyl\|2\|aminoethylsulfonyl amide, another precursor, has been accomplished from cystine.