神经肽的不对称全合成与结构重配

IF 3.6 2区化学 Q1 CHEMISTRY, ORGANIC

Journal of Organic Chemistry Pub Date : 2025-03-19 DOI:10.1021/acs.joc.5c00258

Kunita Phakdeeyothin, Jian-Liang Li, Yi-Tian Hong, Rong-Jie Chein

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引用次数: 0

摘要

我们报道了（+）和（−）两种形式的光学活性神经酮的不对称全合成，这是一种最初于2022年从彩色Nervilia concolor中分离出来的天然产物。从市售间苯二酚开始，光纯神经酮通过10步合成，采用正交定向策略和关键的后期Lewis酸介导的高度非对映选择性还原相结合。在圆二色性（CD）光谱中观察到的差异促使神经蛋白的绝对构型从（3S, 8R）重新分配到（3R, 8S）。

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Asymmetric Total Synthesis and Structural Reassignment of Nervione

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Asymmetric Total Synthesis and Structural Reassignment of Nervione

We report the asymmetric total synthesis of optically active nervione in both (+) and (−) forms, a natural product initially isolated from Nervilia concolor in 2022. Beginning with commercially available resorcinol, optically pure nervione was synthesized in 10 steps, employing a combination of ortho-directed strategies and a crucial late-stage, Lewis acid-mediated, highly diastereoselective reduction. Discrepancies observed in circular dichroism (CD) spectra prompted the reassignment of nervione’s absolute configuration from (3S, 8R) to (3R, 8S).

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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.