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通过区域选择性分子间氧化苯酚偶联实现（-）-二氢愈创木脂素的全合成。

Total Synthesis of (-)-Dimatairesinol via Regioselective Intermolecular Oxidative Phenol Coupling.

作者信息

Chatpreecha Rungrawin, Leowanawat Pawaret, Kuhakarn Chutima, Reutrakul Vichai, Soorukram Darunee

机构信息

Department of Chemistry, Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand.

Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand.

出版信息

Org Lett. 2025 Jul 25;27(29):7756-7761. doi: 10.1021/acs.orglett.5c01942. Epub 2025 Jul 10.

DOI:10.1021/acs.orglett.5c01942
PMID:40639950
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12305652/
Abstract

We report the total synthesis of (-)-dimatairesinol, a new dimeric natural lignan possessing a unique interconvertible biaryl skeleton coupled at C-5/C-5 of two units of dibenzyl γ-butyrolactone lignan, namely, matairesinol. The key step involved high regioselective formation of a C-5/C-5 biaryl bond between two units of chiral phenolic γ-butyrolactone (R = H) via a direct and metal-free oxidative phenol coupling mediated by PIFA. On the contrary, C-6/C-6 biaryl coupling exclusively took place when nonphenolic γ-butyrolactones (R ≠ H) were employed, providing the corresponding biaryl products as atropisomers. Synthetic manipulations on the C-5/C-5-biaryl intermediate led to (-)-dimatairesinol.

摘要

我们报道了（-）-二马特雷辛醇的全合成，它是一种新型二聚体天然木脂素，具有独特的可相互转化的联芳基骨架，在两个二苄基γ-丁内酯木脂素单元（即马特雷辛醇）的C-5/C-5处相连。关键步骤涉及通过PIFA介导的直接无金属氧化酚偶联，在手性酚γ-丁内酯（R = H）的两个单元之间高区域选择性地形成C-5/C-5联芳基键。相反，当使用非酚γ-丁内酯（R≠H）时，仅发生C-6/C-6联芳基偶联，提供相应的作为阻转异构体的联芳基产物。对C-5/C-5-联芳基中间体进行合成操作得到了（-）-二马特雷辛醇。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/41d7/12305652/c258ef6d3c5c/ol5c01942_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/41d7/12305652/c9de2ac67dff/ol5c01942_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/41d7/12305652/635eca07cda2/ol5c01942_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/41d7/12305652/f2aa06fcd767/ol5c01942_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/41d7/12305652/d21d1ce5a9e6/ol5c01942_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/41d7/12305652/c23f0479f38f/ol5c01942_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/41d7/12305652/c258ef6d3c5c/ol5c01942_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/41d7/12305652/c9de2ac67dff/ol5c01942_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/41d7/12305652/635eca07cda2/ol5c01942_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/41d7/12305652/f2aa06fcd767/ol5c01942_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/41d7/12305652/d21d1ce5a9e6/ol5c01942_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/41d7/12305652/c23f0479f38f/ol5c01942_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/41d7/12305652/c258ef6d3c5c/ol5c01942_0006.jpg

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本文引用的文献

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Dalton Trans. 2025 Jan 2;54(2):754-763. doi: 10.1039/d4dt02197e.
2
Chelation-assisted and steric-controlled selectivity in the Pd-catalyzed C-H/C-H oxidative coupling of indoles.钯催化吲哚的C-H/C-H氧化偶联反应中的螯合辅助及空间控制选择性
Chem Commun (Camb). 2024 Nov 5;60(89):13028-13031. doi: 10.1039/d4cc03835e.
3
Total Syntheses and Absolute Stereochemical Correction of Negundin B, Vitexin 1, and Vitexin 6.
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J Org Chem. 2024 Mar 1;89(5):3644-3651. doi: 10.1021/acs.joc.3c02751. Epub 2024 Feb 20.
4
Forsythia velutina Nakai extract: A promising therapeutic option for atopic dermatitis through multiple cell type modulation.忍冬提取物：通过多细胞类型调节治疗特应性皮炎的有前途的治疗选择。
Allergy. 2024 May;79(5):1242-1257. doi: 10.1111/all.15967. Epub 2023 Dec 1.
5
Organocatalytic aldol approach for the protecting group-free asymmetric synthesis of (7')-parabenzlactone, (-)-hinokinin, (-)-yatein, (-)-bursehernin, (-)-pluviatolide, (+)-isostegane and allied lignans.有机催化羟醛缩合方法用于(7')-对苄内酯、(-)-日桧素、(-)-叶下珠素、(-)-紫堇醇灵碱、(-)-雨久花内酯、(+)-异斯替甘和相关木脂素的无保护基不对称合成。
Org Biomol Chem. 2023 Nov 8;21(43):8749-8756. doi: 10.1039/d3ob01446k.
6
Recent advances in oxidative phenol coupling for the total synthesis of natural products.近期在氧化酚偶联反应用于天然产物全合成方面的进展。
Nat Prod Rep. 2024 Feb 21;41(2):208-227. doi: 10.1039/d3np00009e.
7
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J Agric Food Chem. 2023 May 3;71(17):6738-6746. doi: 10.1021/acs.jafc.3c00516. Epub 2023 Apr 21.
8
Atroposelective Synthesis of 2,2'-Bis(arylamino)-1,1'-biaryls by Oxidative Iron(III)- and Phosphoric Acid-Catalyzed C-C Coupling of Diarylamines.通过氧化铁(III)和磷酸催化的二苯胺的 C-C 偶联反应，对映选择性合成 2,2'-双(芳基氨基)-1,1'-联芳基。
Chemistry. 2023 Jan 27;29(6):e202203269. doi: 10.1002/chem.202203269. Epub 2022 Nov 27.
9
Catalytic Oxidative Coupling of Phenols and Related Compounds.酚类及相关化合物的催化氧化偶联
ACS Catal. 2022 Jun 3;12(11):6532-6549. doi: 10.1021/acscatal.2c00318. Epub 2022 May 18.
10
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J Am Chem Soc. 2022 Aug 17;144(32):14864-14873. doi: 10.1021/jacs.2c06240. Epub 2022 Aug 3.