Total synthesis of justicidin B, justicidin E, and taiwanin C: A general and flexible approach toward the synthesis of natural arylnaphthalene lactone lignans

被引：2

作者：

Wei, Kai ^{[1
,2
]}

Sun, Yucui ^{[1
]}

Xu, Yiren ^{[1
]}

Hu, Wen ^{[1
]}

Ma, Ying ^{[1
]}

Lu, Yi ^{[1
]}

Chen, Wen ^{[1
]}

Zhang, Hongbin ^{[1
]}

机构：

[1] Yunnan Univ, Yunnan Prov Ctr Res & Dev Nat Prod, Sch Pharm, Key Lab Med Chem Nat Resource,Minist Educ,Yunnan C, Kunming, Peoples R China

[2] Pingdingshan Univ, Henan Engn Res Ctr Funiu Mt Med Resources Utilizat, Sch Med Sci, Pingdingshan, Peoples R China

来源：

FRONTIERS IN CHEMISTRY | 2022年 / 10卷

关键词：

total synthesis; natural products; arylnaphthalene lactone lignans; Suzuki cross-coupling; cation-induced cyclization; CATALYZED 2+2+2 COCYCLIZATION; RETROJUSTICIDIN-B; BENZANNULATION REACTION; ANTIVIRAL ACTIVITY; CYTOTOXIC LIGNANS; CYCLIZATION; ARYNES; PODOPHYLLOTOXIN; CONDENSATION; HELIOXANTHIN;

D O I：

10.3389/fchem.2022.1103554

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Lignans are widely present in traditional medicinal plants. Many natural arylnaphthalene lactone lignans (NALLs) isolated from the genera Justicia, Haplophyllum, and Phyllanthus possess interesting biological activities. Herein, we report a general strategy for the total synthesis of this kind of lignans. Features of this new approach are an aryl-alkyl Suzuki cross-coupling to introduce the dioxinone unit, a cation-induced cyclization to construct the aryl dihydronaphthalene, and base-mediated oxidative aromatization to furnish the arylnaphthalene core. By incorporating these key transformations, the total syntheses of justicidins B and E and taiwanin C covered type I and type II NALLs were accomplished.

引用

页数：9

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