2011
DOI: 10.1039/c0ob00952k
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Green oxidations of furans—initiated by molecular oxygen—that give key natural product motifs

Abstract: In this article, we explore how changes in the positioning of pendant hydroxyl functionalities in the photooxygenation substrate dramatically alter the course of furan oxidations that are initiated by singlet oxygen; and, how these different reactivities can be harnessed through cascade reaction sequences to access, rapidly and effectively, a broad range of important natural product motifs.

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Cited by 66 publications
(23 citation statements)
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“…Singlet oxygen is an ideal reagent for many reasons; one of the most important is because it fits very well into the modern paradigm which targets greater sustainability in chemistry 8a,c. Not only is this profile due to its intrinsic characteristics (atom economy, selectivity etc.…”
Section: Methodsmentioning
confidence: 99%
“…Singlet oxygen is an ideal reagent for many reasons; one of the most important is because it fits very well into the modern paradigm which targets greater sustainability in chemistry 8a,c. Not only is this profile due to its intrinsic characteristics (atom economy, selectivity etc.…”
Section: Methodsmentioning
confidence: 99%
“…By employing such strategies we have been able to synthesise large sections from a number of highly oxygenated natural products (right hand side, Scheme ); for example, the A‐E rings of pectenotoxins, A‐D rings of azaspiracids, the [6,6,5]‐bis‐spiroketal unit of salinomycin. Traditional syntheses of these types of oxygen‐rich compounds are inherently rife with nonstrategic redox reactions and protecting group manipulations.…”
Section: What Is Your Current Research Focus and Why Is It Important?mentioning
confidence: 99%
“…On the other hand, spirocompounds have also attracted the attention of organic and medicinal chemists because of their broad spectrum of biological activities . Hence, their synthesis continues to attract attention and provides an interesting challenge . In the literature, there is not much research related to the synthesis of spiropyrazole derivatives, even though they also have biological activities .…”
Section: Introductionmentioning
confidence: 99%