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-双环[6.1.0]壬炔羧酸的简洁合成

A concise synthesis of -bicyclo[6.1.0]nonyne carboxylic acid.

作者信息

Weir Mackenzie, Vaccari Beatrice, Matthews Aidan, Turnbull Graeme, Kozhevnikov Valery N

机构信息

Department of Applied Sciences, Northumbria University Ellison Building Newcastle upon Tyne NE1 8ST UK

Dipartimento di Chimica dell'Università degli Studi di Milano Via C. Golgi 19 I-20133 Milan Italy.

出版信息

RSC Adv. 2024 Nov 21;14(50):37400-37403. doi: 10.1039/d4ra06708h. eCollection 2024 Nov 19.

DOI:10.1039/d4ra06708h
PMID:39575366
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11580154/
Abstract

Bicyclo[6.1.0]nonyne carboxylic acid (BCN-COOH) is a valuable intermediate for the development of bioorthogonal click reagents. A convenient three-step synthesis of pure diastereomer -BCN-COOH is reported here, with an overall yield of 32% starting from 1,5-cyclooctadiene. To the best of our knowledge, this is the shortest route to -BCN-COOH known to date. The new method compares favourably with the optimised four-step synthesis based on previously reported data.

摘要

双环[6.1.0]壬炔羧酸（BCN - COOH）是用于开发生物正交点击试剂的重要中间体。本文报道了一种便捷的三步合成纯非对映异构体-BCN - COOH的方法，以1,5 - 环辛二烯为起始原料，总收率为32%。据我们所知，这是迄今为止已知的合成-BCN - COOH的最短路线。与基于先前报道数据的优化四步合成法相比，新方法具有优势。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/54aa/11580154/78f04f574cf2/d4ra06708h-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/54aa/11580154/78f04f574cf2/d4ra06708h-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/54aa/11580154/78f04f574cf2/d4ra06708h-s1.jpg

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本文引用的文献

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Site-Selective Protein Conjugation by a Multicomponent Ugi Reaction.通过多组分乌吉反应进行位点选择性蛋白质缀合
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Catching up with tetrazines: coordination of Re(I) to 1,2,4-triazine facilitates an inverse electron demand Diels-Alder reaction with strained alkynes to a greater extent than in corresponding 1,2,4,5-tetrazines.
追赶上四嗪：铼（I）与1,2,4-三嗪的配位比在相应的1,2,4,5-四嗪中更能促进与张力炔烃的逆电子需求狄尔斯-阿尔德反应。
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