Studies Toward the Enantiospecific Total Synthesis of Rhodexin A

Jung, Michael E.; Guzaev, Mikhail

doi:10.1021/jo400909t

Cited by 22 publications

(13 citation statements)

References 54 publications

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“…In later work, this key intermediate has been brought forward to rhodexin A [102] and three other analogues [103] by the same group,a nd in additional work, the authors make use of am ore hindered diene,w hich necessitatest he use of stronger Lewis acids and highert emperatures. [104]…”

Section: Rhodexin Amentioning

confidence: 99%

“…The reaction proceeds cleanly and gives the key intermediate, tricyclic compound 83 , in 86 % yield. In later work, this key intermediate has been brought forward to rhodexin A and three other analogues by the same group, and in additional work, the authors make use of a more hindered diene, which necessitates the use of stronger Lewis acids and higher temperatures …”

Section: Applications Of Iedda Reactionsmentioning

confidence: 99%

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Inverse‐Electron‐Demand Diels–Alder Reactions: Principles and Applications

Png

Zeng

et al. 2017

Chemistry An Asian Journal

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Inverse-electron-demand Diels-Alder (iEDDA) reactions are an intriguing class of cycloaddition reactions that have attracted increasing attention for their application in bioorthogonal chemistry, the total synthesis of natural products, and materials science. In many cases, the application of the iEDDA reaction has been demonstrated as an innovative approach to achieve target structures. The theoretical aspects of this class of reactions are of particular interest for scientists as a means to understand the various factors, such as steric strain and electron density of the attached groups, that govern the reaction and thus to elucidate the reaction mechanism. This review aims to summarize both theoretical investigations and application-driven research work on the iEDDA reaction. First, the historical aspects and the theoretical basis of the reaction, especially recent advances in time-dependent density functional theory (TD-DFT) calculations, as well as catalysis strategies will be highlighted and discussed. Second, the applications of this novel reaction in the context of materials science, bioorthogonal chemistry, and total synthesis of natural products will be elaborated with selected recent examples. The challenges and opportunities of the iEDDA reaction will be highlighted to give more insight into its potential applications in many other research areas.

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Section: Rhodexin Amentioning

confidence: 99%

Section: Applications Of Iedda Reactionsmentioning

confidence: 99%

Inverse‐Electron‐Demand Diels–Alder Reactions: Principles and Applications

Png

Zeng

et al. 2017

Chemistry An Asian Journal

View full text Add to dashboard Cite

show abstract

“…Therefore, we next tried to use ozonolosis to remove two extra carbon atoms. The enolization of 24 was achieved in a regioselective manner, but the oxidative cleavage was more complicated than expected: Apart from the desired aldehyde 27 , hydroxy ketone 26 was also obtained . However, 26 could be transformed into 27 by sequential treatment with NaBH 4 and NaIO 4 and thus could be recycled.…”

Section: Figurementioning

confidence: 99%

Efficient Synthetic Routes to (±)‐Hippolachnin A, (±)‐Gracilioethers E and F and the Alleged Structure of (±)‐Gracilioether I

2017

Chemistry A European J

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“…Rhodexin A ( 56 ) is a cardiac glycoside and is also very active against human leukaemia K562 cells 24. Jung et al25a reported the first total synthesis of rhodexin A in 2011, and the same group has also recently assembled the tetracyclic core of rhodexin A enantiospecifically through a highly hindered inverse‐electron‐demand Diels–Alder reaction 25b. Optically pure Wieland–Miescher ketone ( 47 ) and pure ( S )‐carvone ( 49 ) were used as chiral starting materials (Scheme ).…”

Section: Synthesis Of Natural and Synthetic Steroids Starting Frommentioning

confidence: 99%

Explosive Decomposition of a Melamine–Cyanuric Acid Supramolecular Assembly for Fabricating Defect‐Rich Nitrogen‐Doped Carbon Nanotubes with Significantly Promoted Catalysis

Zhao

Dai

et al. 2015

Chemistry A European J

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A facile and scalable approach for fabricating structural defect-rich nitrogen-doped carbon nanotubes (MCSA-CNTs) through explosive decomposition of melamine-cyanuric acid supramolecular assembly is presented. In comparison to pristine carbon nanotubes, MCSA-CNT exhibits significantly enhanced catalytic performance in oxidant- and steam-free direct dehydrogenation of ethylbenzene, demonstrating the potential for metal-free clean and energy-saving styrene production. This finding also opens a new horizon for preparing highly-efficient carbocatalysts rich in structural defect sites for diverse transformations.

show abstract

Studies Toward the Enantiospecific Total Synthesis of Rhodexin A

Cited by 22 publications

References 54 publications

Inverse‐Electron‐Demand Diels–Alder Reactions: Principles and Applications

Inverse‐Electron‐Demand Diels–Alder Reactions: Principles and Applications

Efficient Synthetic Routes to (±)‐Hippolachnin A, (±)‐Gracilioethers E and F and the Alleged Structure of (±)‐Gracilioether I

Explosive Decomposition of a Melamine–Cyanuric Acid Supramolecular Assembly for Fabricating Defect‐Rich Nitrogen‐Doped Carbon Nanotubes with Significantly Promoted Catalysis

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