Functionatization of diazotetronic acid and application in a stereoselective modular synthesis of pulvinone, aspulvinones A-E, G, Q and their analogues

被引：11

作者：

Manchoju, Amarender ^{[1
]}

Annadate, Ritesh A. ^{[1
]}

Desquien, Lise ^{[1
]}

Pansare, Sunil V. ^{[1
]}

机构：

[1] Mem Univ, Dept Chem, St John, NF A1B 3X7, Canada

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2018年 / 16卷 / 34期

基金：

加拿大自然科学与工程研究理事会; 加拿大创新基金会;

关键词：

ASPERGILLUS-TERREUS; TETRONIC ACIDS; ANTIBACTERIAL ACTIVITY; DIAZO-COMPOUNDS; DERIVATIVES; BIOSYNTHESIS; INHIBITORS; PIGMENTS; FUNGI; CONDENSATION;

D O I：

10.1039/c8ob01511b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A modular synthesis of aspulvinones A, B, C, D, E, G and the recently isolated aspulvinone Q was developed. The methodology features a highly stereoselective aldol condensation of diazotetronic acid with aldehydes to provide 5-arylidene diazotetronates. Subsequent catalytic intermolecular C-H insertion reactions of the arylidene tetronates with arenes provide a series of naturally occurring aspulvinones including aspulvinones C, D and Q which have not been synthesized before. Variation of the aldehyde and the arene components furnishes synthetic analogues of the aspulvinones.

引用

收藏

页码：6224 / 6238

页数：15

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