Asymmetric Total synthesis of Asperones A and B through Organocatalyzed Quinone [5+2] Cycloaddition

被引：0

作者：

Qu, Chunlei ^{[1
,2
]}

Chen, Lu ^{[1
,2
]}

Wang, Peng ^{[1
,2
]}

Zhang, Jingwei ^{[1
,2
]}

Ding, Yiming ^{[1
,2
]}

Long, Xianwen ^{[1
,2
]}

Zhang, Tingrong ^{[1
,2
]}

Zhao, Yaqiu ^{[3
]}

Deng, Jun ^{[1
,2
]}

机构：

[1] Nankai Univ, Coll Chem, Frontiers Sci Ctr New Organ Matter, State Key Lab, Tianjin 300071, Peoples R China

[2] Nankai Univ, Inst Elementoorgan Chem, Coll Chem, Frontiers Sci Ctr New Organ Matter, Tianjin 300071, Peoples R China

[3] China Acad Chinese Med Sci, Natl Resource Ctr Chinese Mat Med, State Key Lab Qual Ensurance & Sustainable Use Dao, Beijing 100700, Peoples R China

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2025年 / 147卷 / 08期

基金：

中国博士后科学基金; 中国国家自然科学基金;

关键词：

DIELS-ALDER REACTION; ALPHA; BETA-UNSATURATED KETONES; MICHAEL ADDITION; A-D; (-)-ELISAPTEROSIN-B; CATALYSIS; YNOLIDES; STEPS;

D O I：

10.1021/jacs.4c16252

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first asymmetric total synthesis of the anti-inflammatory polyketides asperones A (1) and B (2) has been accomplished. Key synthetic steps include a Diels-Alder and retro-Diels-Alder cascade to construct the poly substituted phenol, an Al-Salen-catalyzed asymmetric cyanosilylation to form the tertiary alcohol of gregatin A, and an organocatalyzed intermolecular [5 + 2] cycloaddition of p-quinone with electron-deficient alkenes to build the crucial [3.2.1] octane core of asperones A (1) and B (2).

引用

页码：6739 / 6746

页数：8

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