Extensions of the Tricyclooctanone Concept. A General Principle for the Synthesis of Linearly and Angularly Annelated Triquinanes

Demuth, Martin; Hinsken, W.

doi:10.1002/anie.198509731

Cited by 34 publications

(5 citation statements)

References 10 publications

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“…In addition, its oxa-and aza-variants have become popular, as shown in an impressive synthesis by Demuth and co-workers, who used the formed cyclopropane to build the tricyclic core of triquinane alkaloids (Figure 4). 53…”

Section: Sensitized Rearrangements and Fragmentationsmentioning

confidence: 99%

Triplet Energy Transfer Photocatalysis: Unlocking the Next Level

Strieth‐Kalthoff

Glorius

2020

Chem

417

262

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Section: Sensitized Rearrangements and Fragmentationsmentioning

confidence: 99%

Triplet Energy Transfer Photocatalysis: Unlocking the Next Level

Strieth‐Kalthoff

Glorius

2020

Chem

417

262

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“…Photochemistry, simulating the natural photosynthesis to use sunlight to drive multifarious chemical transformations, is of great practical significance for the development of sustainable energy. Among them, energy-transfer (EnT) photocatalysis has emerged as a gentle and selective approach to access highly reactive triplet states through indirect excitation and achieved a series of special transformations, such as cycloadditions, rearrangements, fragmentations, especially geometrical isomerization of alkenes, and sensitization of organometallic intermediates . In this process, a photosensitizer (PS) with excellent photostability, powerful absorption, and higher energy of the triplet state than the substrate is the basis for realizing more extensive applications in drug synthesis and the chemical industry .…”

Section: Introductionmentioning

confidence: 99%

Energy-Transfer-Mediated Photocatalysis by a Bioinspired Organic Perylenephotosensitizer HiBRCP

Zhang

Xia

et al. 2021

J. Org. Chem.

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Energy transfer plays a special role in photocatalysis by utilizing the potential energy of the excited state through indirect excitation, in which a photosensitizer determines the thermodynamic feasibility of the reaction. Bioinspired by the energy-transfer ability of natural product cercosporin, here we developed a green and highly efficient organic photosensitizer HiBRCP (hexaisobutyryl reduced cercosporin) through structural modification of cercosporin. After structural manipulation, its triplet energy was greatly improved, and then, it could markedly promote the efficient geometrical isomerization of alkenes from the E-isomer to the Z-isomer. Moreover, it was also effective for energy-transfer-mediated organometallic catalysis, which allowed realization of the cross-coupling of aryl bromides and carboxylic acids through efficient energy transfer from HiBRCP to nickel complexes. Thus, the study on the relationship between structural manipulation and their photophysical properties provided guidance for further modification of cercosporin, which could be applied to more meaningful and challenging energy-transfer reactions.

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“…Bicyclo[2.2.2]octenones can be obtained via the Diels–Alder reactions of suitably substituted cyclohexa-2,4-dienones with appropriate dienophiles. These useful bicyclic synthons can be converted into polysubstituted cyclohexanes, bicyclo[3.2.1]octenones, bicyclo[4.2.0]octenones, fused triquinanes, cis -decalins, and bicyclo[4.2.2]decenones . 6,6-Dialkoxycyclohexa-2,4-dienones, named as orthoquinone monoketals or masked o -benzoquinones (MOBs), are a synthetically useful class of 2,4-cyclohexadienones.…”

Section: Introductionmentioning

confidence: 99%