Asymmetric Total Synthesis and Structural Reassignment of Nervione

被引：0

作者：

Phakdeeyothin, Kunita ^{[1
]}

Li, Jian-Liang ^{[2
]}

Hong, Yi-Tian ^{[3
]}

Chein, Rong-Jie ^{[1
]}

机构：

[1] Acad Sinica, Inst Chem, Taipei 11529, Taiwan

[2] Natl Taiwan Univ, Dept Chem, Taipei 10617, Taiwan

[3] Natl Taiwan Normal Univ, Dept Chem, Taipei 11677, Taiwan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2025年 / 90卷 / 12期

关键词：

ABSOLUTE-CONFIGURATION; DIASTEREOSELECTIVE REDUCTION; GLYCOSIDES; PLANT; ACIDS; METHODOLOGY; INDOLES;

D O I：

10.1021/acs.joc.5c00258

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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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页码：4389 / 4396

页数：8

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