氧化自由基环化三环前列腺素D2代谢产物甲酯的不对称全合成。

IF 2.1 4区化学 Q2 CHEMISTRY, ORGANIC

Beilstein Journal of Organic Chemistry Pub Date : 2025-09-24 eCollection Date: 2025-01-01 DOI:10.3762/bjoc.21.152

Miao Xiao, Liuyang Pu, Qiaoli Shang, Lei Zhu, Jun Huang

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引用次数: 0

摘要

前列腺素D2 （PGD2）是许多人类疾病和生物学途径的关键病理生理介质。三环前列腺素D2代谢物甲酯（Tricyclic - pgdm methyl ester）是尿中PGD2的主要代谢物，可作为PGD2过量产生的临床指标。然而，三环- pgdm甲酯的可用量有限，阻碍了其实际应用，需要三环- pgdm甲酯的合成方法。利用氧化自由基环化技术立体选择性地合成了具有三个连续立体中心的环戊醇亚基，通过9步合成了三环- pgdm甲酯，总产率为8%。

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Asymmetric total synthesis of tricyclic prostaglandin D2 metabolite methyl ester via oxidative radical cyclization.

Prostaglandin D₂ (PGD₂) is a key pathophysiological mediator in many human diseases and biological pathways. Tricyclic prostaglandin D₂ metabolite methyl ester (tricyclic-PGDM methyl ester), the major urinary metabolite of PGD₂, can be used as a clinical indicator for PGD₂ overproduction. However, the limited amount of tricyclic-PGDM methyl ester available has prevented its practical use, and synthesis methods for tricyclic-PGDM methyl ester are required. Based on the utilization of oxidative radical cyclization for the stereoselective construction of the cyclopentanol subunit with three consecutive stereocenters, we describe an asymmetric total synthesis of tricyclic-PGDM methyl ester in 9 steps and 8% overall yield.

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来源期刊

Beilstein Journal of Organic Chemistry 化学-有机化学

CiteScore

4.90

自引率

3.70%

发文量

167

审稿时长

1.4 months

期刊介绍： The Beilstein Journal of Organic Chemistry is an international, peer-reviewed, Open Access journal. It provides a unique platform for rapid publication without any charges (free for author and reader) – Platinum Open Access. The content is freely accessible 365 days a year to any user worldwide. Articles are available online immediately upon publication and are publicly archived in all major repositories. In addition, it provides a platform for publishing thematic issues (theme-based collections of articles) on topical issues in organic chemistry. The journal publishes high quality research and reviews in all areas of organic chemistry, including organic synthesis, organic reactions, natural product chemistry, structural investigations, supramolecular chemistry and chemical biology.