全合成微磷酰胺A的Fmoc-threo-HOAsn的不对称合成。

IF 2.7 3区化学 Q1 CHEMISTRY, ORGANIC Organic & Biomolecular Chemistry Pub Date : 2025-03-19 DOI:10.1039/D5OB00297D

Fangfang Bian, Jiarong Jiao, Qian Gong, Zhitao Chen and Delin Chen

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引用次数: 0

摘要

受fmoc保护的β-羟基天冬酰胺是有机化学中重要的结构基序，广泛存在于天然产物和抗生素等临床重要药物中。本研究开发了一种由简单的加纳醛非对对选择性合成fmoc保护的HOAsn的方法。Fmoc保护的加纳醛与三苯基甲基异氰酸和甲酸在60℃下反应，产率高，非对映选择性好。还报道了将Passerini反应产物fmoc保护的HOAsn用于Fmoc-SPPS在合成微磷酰胺A及其类似物中的应用，这有利于系统的SAR研究。

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Asymmetric synthesis of Fmoc-threo-HOAsn for the total synthesis of nicrophorusamide A†

Fmoc-protected β-hydroxyasparagine is an essential structural motif in organic chemistry, widely present in natural products and clinically important drugs, such as antibiotics. Here, a diastereoselective synthesis of Fmoc-protected HOAsn from a simple Garner's aldehyde has been developed. The Fmoc protected Garner's aldehyde reacted with triphenylmethyl isocyanide and formic acid at 60 °C, affording good yield with excellent diastereoselectivity. The application of the Passerini reaction product Fmoc-protected HOAsn for Fmoc-SPPS towards the synthesis of nicrophorusamide A and its analogues has also been reported, which is conducive to systematic SAR studies.

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来源期刊

Organic & Biomolecular Chemistry 化学-有机化学

CiteScore

5.50

自引率

9.40%

发文量

1056

审稿时长

1.3 months

期刊介绍： Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.