A concise synthesis of herbertenolide

被引：2

作者：

Hu, Jiadong ^{[1
]}

Ji, Kai ^{[2
]}

Yan, Lihong ^{[2
]}

Yang, Siyu ^{[2
]}

Li, Yin ^{[2
]}

Wen, Wen ^{[1
]}

Chen, Le ^{[2
]}

Wu, Xiaohui ^{[2
]}

Hu, Youcai ^{[3
]}

Xie, Weiqing ^{[2
,4
]}

机构：

[1] Yangling Vocat & Tech Coll, Sch Med & Chem Engn, 24 Weihui Rd, Yangling 712100, Shaanxi, Peoples R China

[2] Northwest A&F Univ, Sch Pharm & Chem, Shaanxi Key Lab Nat Prod & Chem Biol, 22 Xinong Rd, Yangling 712100, Shaanxi, Peoples R China

[3] Chinese Acad Med Sci, Peking Union Med Coll, Inst Mat Med, State Key Lab Bioact Subst & Funct Nat Med, Beijing, Peoples R China

[4] Key Lab Bot Pesticide R&D Shaanxi Prov, Yangling 712100, Shaanxi, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2022年 / 20卷 / 11期

基金：

中国国家自然科学基金;

关键词：

CARBON CENTERS; CONSTRUCTION; SESQUITERPENOIDS; (+/-)-HERBERTENOLIDE; GENERATION; REACTIVITY; PALLADIUM;

D O I：

10.1039/d2ob00041e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise synthesis of (+/-)-herbertenolide has been accomplished herein. The strategy relies on a H2O2-mediated oxidative ring contraction of all-substituted cyclic alpha-formyl ketones for the stereospecific construction of contiguous quaternary carbon centers (CQCCs). Furthermore, a Sc(OTf)(3)/chiral N,N '-dioxide catalyzed asymmetric Michael addition of benzofuranone to MVK has been optimized for forging a chiral aromatic quaternary carbon center, which enables the formal synthesis of (+)-ent-herbertenolide.

引用

页码：2205 / 2208

页数：4

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