通过立体异构体的全合成修订松呋喃酮毒素 A 结构的建议

IF 2.5 4区医学 Q3 CHEMISTRY, MEDICINAL

Journal of Natural Medicines Pub Date : 2024-04-08 DOI:10.1007/s11418-024-01810-5

Kazuki Ujiie, Chiaki Tanaka, Masayoshi Arai, Masaru Hashimoto, Yuki Yoshida, Tomikazu Kawano, Satoru Tamura

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引用次数: 0

摘要

Evidente 等人于 2021 年分离出了具有反式环氧侧链的α-亚烷基-β-羟基-γ-甲基-γ-丁内酯（α-alkylidene-β-hydroxy-γ-methyl-γ-butyrolactone），并通过基于 DFT 的光谱再研究和立体控制合成对其中环氧官能团的相对构型进行了修正。本研究表明，构象灵活的无环侧链上的立体中心很难从构型上加以阐明。Sharpless 的对映体选择性环氧化反应和二羟基化反应对构型的再研究相当有效。由于我们的合成可以得到所有非对映异构体，因此在下一步的结构-生物活性关系研究中将非常有效。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Proposal for structure revision of pinofuranoxin A through total syntheses of stereoisomers

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Proposal for structure revision of pinofuranoxin A through total syntheses of stereoisomers

The relative configuration of the epoxide functionality in pinofuranoxin A (1), α-alkylidene-β-hydroxy-γ-methyl-γ-butyrolactone with trans-epoxy side chain isolated by Evidente et al. in 2021, was revised by DFT-based spectral reinvestigations and stereo-controlled synthesis. The present investigation demonstrates the difficulty of the configurational elucidation of the stereogenic centers on the conformationally flexible acyclic side-chains. Sharpless’s enantioselective epoxidations and dihydroxylations were quite effective in the reinvestigations of the configurations. As our syntheses made all diastereomers available, these would be quite effective in the next structure-biological activity relationship studies.

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来源期刊

Journal of Natural Medicines 医学-药学

CiteScore

6.90

自引率

3.00%

发文量

审稿时长

1.7 months

期刊介绍： The Journal of Natural Medicines is an international journal publishing original research in naturally occurring medicines and their related foods and cosmetics. It covers: -chemistry of natural products -biochemistry of medicinal plants -pharmacology of natural products and herbs, including Kampo formulas and traditional herbs -botanical anatomy -cultivation of medicinal plants. The journal accepts Original Papers, Notes, Rapid Communications and Natural Resource Letters. Reviews and Mini-Reviews are generally invited.