Enantioselective Synthesis of Arene cis-Dihydrodiols from 2-Pyrones

被引：37

作者：

Liang, Xiao-Wei ^{[1
,2
]}

Zhao, Yunlong ^{[1
,2
]}

Si, Xu-Ge ^{[1
,2
]}

Xu, Meng-Meng ^{[1
,2
]}

Tan, Jia-Hao ^{[1
,2
]}

Zhang, Zhi-Mao ^{[1
,2
]}

Zheng, Cheng-Gong ^{[1
,2
]}

Zheng, Chao ^{[3
]}

Cai, Quan ^{[1
,2
]}

机构：

[1] Fudan Univ, Dept Chem, 220 Handan Rd, Shanghai 200433, Peoples R China

[2] Fudan Univ, Res Ctr Mol Recognit & Synth, 220 Handan Rd, Shanghai 200433, Peoples R China

[3] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2019年 / 58卷 / 41期

基金：

中国国家自然科学基金;

关键词：

asymmetric catalysis; Diels-Alder reaction; dihydrodiols; retro-Diels-Alder reactions; total synthesis; DIELS-ALDER REACTIONS; CHEMOENZYMATIC TOTAL-SYNTHESIS; ELECTRONICALLY MATCHED 2-PYRONES; ENZYMATIC DIHYDROXYLATION; AROMATIC-HYDROCARBONS; OXIDATIVE-DEGRADATION; OXYGENATED AROMATICS; ASYMMETRIC-SYNTHESIS; MICROBIAL OXIDATION; METHYL COUMALATE;

D O I：

10.1002/anie.201908284

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An enantioselective chemical synthesis of arene cis-dihydrodiols has been realized from 2-pyrones through sequential ytterbium-catalyzed asymmetric inverse-electron-demand Diels-Alder (IEDDA) reaction of 2-pyrones and retro-Diels-Alder extrusion of CO2. By using this strategy, a series of substituted arene cis-dihydrodiols can be obtained efficiently with high enantioselectivity (>99 % ee in many cases). Based on this strategy, efficient and concise asymmetric total syntheses of (+)-MK7607 and 1-epi-(+)-MK7607 were accomplished.

引用

页码：14562 / 14567

页数：6

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