丁烯内酯直接功能化片内酯A和B的全合成及其生物学评价

IF 3.3 2区化学 Q1 CHEMISTRY, ORGANIC

Journal of Organic Chemistry Pub Date : 2026-10-20 DOI:10.1021/acs.joc.6c01907

Yuto Fuse,Hwanhee Moon,Ryuji Kouda,Kensyo Inoue,Haruna Shimura,Satoshi Ohte,Sena Fujisawa,Yuya Miyoshi,Masaharu Saito,Taichi Ohshiro,Tohru Nagamitsu,Masaki Ohtawa

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引用次数: 0

摘要

片内酯A和B是含有氧化丁烯内酯框架的假区域异构体天然产物，在进行性骨化性纤维发育不良（FOP）的背景下引起了人们的兴趣。我们通过镍催化碘化烷基与α-和β-溴丁烯内酯的还原偶联首次实现了全合成。对烷基亲电试剂的初步研究表明，这种偶联可以应用于简单的伯、仲烷基碘化物。该方法还提供了类似物来比较γ-取代对骨形态发生蛋白（BMP）诱导的碱性磷酸酶抑制和细胞毒性的影响。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Total Syntheses and Biological Evaluation of Lamellolactones A and B via Direct Butenolide Functionalization

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Total Syntheses and Biological Evaluation of Lamellolactones A and B via Direct Butenolide Functionalization

Lamellolactones A and B are pseudoregioisomeric natural products bearing oxidized butenolide frameworks and have attracted interest in the context of fibrodysplasia ossificans progressiva (FOP). We achieved their first total syntheses via Ni-catalyzed reductive coupling of a common alkyl iodide with α- and β-bromobutenolides. A preliminary examination of alkyl electrophiles indicated that the coupling could be applied to simple primary and secondary alkyl iodides. The route also furnished analogues for comparison of γ-substitution effects on bone morphogenetic protein (BMP)-induced alkaline phosphatase inhibition and cytotoxicity.

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来源期刊

Journal of Organic Chemistry 化学-有机化学

CiteScore

6.20

自引率

11.10%

发文量

1467

审稿时长

2 months

期刊介绍： Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.