Total Synthesis of Rhodonoids A, B, E, and F, Enabled by Singlet Oxygen Ene Reactions

被引：17
|
作者：
Burchill, Laura [1 ]
George, Jonathan H. [1 ]
机构：
[1] Univ Adelaide, Dept Chem, Adelaide, SA 5005, Australia
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 04期
基金：
澳大利亚研究理事会;
关键词：
BIOMIMETIC TOTAL-SYNTHESIS; (+/-)-RHODONOIDS; PAIRS;
D O I：
10.1021/acs.joc.9b02968
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Singlet oxygen is a versatile reagent for the selective oxidation of organic compounds under mild reaction conditions. It is frequently invoked in biosynthetic pathways, so it is especially suitable for application in the biomimetic synthesis of natural products. Herein, we show that use of the singlet oxygen ene reaction, combined with [2 + 2] cycloadditions, leads to concise, divergent, and redox-economic total syntheses of several polycyclic members of the rhodonoid family of meroterpenoids.
引用
收藏
页码：2260 / 2265
页数：6
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