利用含硼異腈合成depsipeptide衍生物

自從發現含硼的Passerini反應以來，報導主要集中在將含硼的羧酸或醛作為唯一的結構單元。部分原因是由於通常將含硼異氰酸酯視為不穩定的材料，不適合合成應用。這項研究提供了證據，證明含硼異氰酸酯足夠穩定，可以用作原料。此外，異氰基可用於多種合成目的，這使其成為有機化學家非常有價值的官能團。在此，描述了利用含硼異氰酸酯合成硼二肽的方法。通過Passerini三組分反應（P-3CR）合成目標化合物，其中H2O被用作溶劑。此外，與通常需要路易斯酸催化劑的常規P-3CR不同，所報導的方法不需要催化劑，並且可以在室溫下進行。各種醛和酸被用作生成所需產物的基礎。

關鍵字

帕瑟里尼反應；多組成反應；硼酸；微波

並列摘要

Since the discovery of the boron-containing Passerini reaction, reports are mainly focusing on having boron-containing carboxylic acids or aldehydes as the only building blocks. This is partly due to the fact that boron-containing isocyanides are generally perceived as the unstable materials that are not suitable for synthetic applications. This study provided evidence that boron-containing isocyanide is stable enough that can be used as the starting material. Further, isocyano group could serve multiple synthetic purposes that make it very valuable functional group for the organic chemists (Scheme 1). Herein, the synthesis of borodepsipeptides utilizing boron-containing isocyanide is described. The target compounds were synthesized via Passerini three component reaction (P-3CR), in which H2O was uti-lized as the solvent. Further, unlike conventional P-3CR, where Lewis acid catalysts are often required, the reported method requires no cata-lyst and proceeds in room temperature. A variety of aldehydes and ac-ids were used as the building blocks to generate the desired products.

並列關鍵字

Passerini ； Multicomponent Reaction ； Boronic Acid ； Microwave

參考文獻

1 IUPAC, Compendium of Chemical Terminology, 2nd ed. (the “Gold Book”) (1997). Online corrected version: (1995) “depsipeptides”

Google Scholar

2 Haste Nina M; Perera, Varahenage R; Maloney, Katherine N; Tran, Dan N; Jensen, Paul; Fenical, William; Nizet, Victor; Hensler, Mary E. Journal of Antibiotics. 2010, 63 (5) 219.