Perylenequinones: Isolation, Synthesis, and Biological Activity

Mulrooey, Carol A; O’Brien, Erin M.; Morgan, Barbara J.; Kozlowski, Marisa C.

doi:10.1002/ejoc.201200184

Cited by 70 publications

(60 citation statements)

References 111 publications

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“…For example, a number of these conditions proved to be suitable for the decarboxylation of advanced intermediates in the total syntheses of hypocrellin A, 44,45 (+)-phleichrome, 46 and other perylenequinone natural products. 47,48 …”

Section: Palladium Promoted Processmentioning

confidence: 99%

Mild Aromatic Palladium-Catalyzed Protodecarboxylation: Kinetic Assessment of the Decarboxylative Palladation and the Protodepalladation Steps

et al. 2013

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Mechanism studies of a mild palladium catalyzed decarboxylation of aromatic carboxylic acids are described. In particular, reaction orders and activation parameters for the two stages of the transformation were determined. These studies guided development of a catalytic system capable of turnover. Further evidence reinforces that the second stage, protonation of the aryl palladium intermediate, is the rate-determining step of the reaction. The first step, decarboxylative palladation is proposed to occur through an intramolecular electrophilic palladation pathway, which is supported by computational and mechansim studies. In contrast to the reverse reaction (C-H insertion), the data support an electrophilic aromatic substitution mechanism involving a stepwise intramolecular protonation sequence for the protodepalladation portion of the reaction.

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Section: Palladium Promoted Processmentioning

confidence: 99%

Mild Aromatic Palladium-Catalyzed Protodecarboxylation: Kinetic Assessment of the Decarboxylative Palladation and the Protodepalladation Steps

et al. 2013

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“…[1] Oxidized derivatives (e.g., perylenequinones 2 [2] ) and partially hydrogenated perylenes [3] have occasionally been used. [1] Oxidized derivatives (e.g., perylenequinones 2 [2] ) and partially hydrogenated perylenes [3] have occasionally been used.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of cis‐ and trans‐Configured Octahydroperylenes

2017

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Lewis acid catalysed dimerization of 5‐methoxy‐1,2,3,4‐tetrahydronaphthalen‐1‐ol yields 4,10‐dimethoxy‐1,2,3,6b,7,8,9,12b‐octahydroperylene, in which the hydrogen atoms at the 6b‐ and 12b‐positions are trans‐arranged. This isomer is less stable than the corresponding cis isomer. Conversion of the trans‐configured meso compound into the racemic cis isomer is possible by heating with a radical initiator to give an anthracene derivative, which is then reduced under Birch conditions. The energetic course of these reactions was investigated with DFT calculations.

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“…Currently, special interest is being applied to the photoactivation of their bioactivity on different targets, including most recently on isozymes of protein kinase C (Mulrooney et al, 2012). Currently, special interest is being applied to the photoactivation of their bioactivity on different targets, including most recently on isozymes of protein kinase C (Mulrooney et al, 2012).…”

Section: Perspectivesmentioning

confidence: 99%

Pigments of Living Fossil Crinoids

Debitus¹,

Kornprobst²

2014

Outstanding Marine Molecules

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Stalked crinoids were, for a long time, known as fossils found in different quarries, and also from ocean depths since the great expeditions of the eighteenth century. The chemical analyses of fossils and also of living organisms led to the discovery of new bioactive pigments, and also confirmed that the core structures of these pigments had been preserved during the fossilization process. The existence of these quinoid pigments also leads to several interesting questions related to their stereochemistry and the photoactivation of their bioactivity.

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Perylenequinones: Isolation, Synthesis, and Biological Activity

Cited by 70 publications

References 111 publications

Mild Aromatic Palladium-Catalyzed Protodecarboxylation: Kinetic Assessment of the Decarboxylative Palladation and the Protodepalladation Steps

Mild Aromatic Palladium-Catalyzed Protodecarboxylation: Kinetic Assessment of the Decarboxylative Palladation and the Protodepalladation Steps

Synthesis of cis‐ and trans‐Configured Octahydroperylenes

Pigments of Living Fossil Crinoids

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