Oxidative Semisynthesis of Natural Products with DMDO

Faisal, Muhammad; Larik, Fayaz Ali; Saeed, Aamer; Shah, Azhar Hussain; Channar, Pervaiz Ali; Khan, Sajjad Ahmad; Ali, M. Rejwan; Kumar, Raj

doi:10.2174/1385272822666180827142304

Cited by 5 publications

(8 citation statements)

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“…17 An updated survey of scientific progress including pioneering developments is essential for further growth of this research area. Although a significant number of reviews are available, 2,[18][19][20] the present review is a compiled collection of research done in the area that covers all aspects of dioxirane-mediated chemistry.…”

Section: Mcgrath'smentioning

confidence: 99%

“…42 This Oxone®-acetone system was explored for various 9-mediated catalytic oxidations like the stereospecific epoxidation of cis-and trans-cinnamic acids (13 and 15) to the corresponding cis-and trans-epoxides (14 and 16) (Scheme 3b and c), respectively, and the oxidation of p-tolyl phenyl sulfoxide 17 to sulfone 18 (Scheme 3d). 39 Mechanistically, the reaction of caroate (12) with a ketone (19) purportedly proceeds through the rapid formation of a peroxo-adduct 20 (Scheme 4). 38,43,44 Then, the acidic proton in 20 is readily deprotonated in a basic medium via rapid proton transfer to yield oxo-anion 22.…”

Section: Generation Isolation and Characterization Of Dioxiranesmentioning

confidence: 99%

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Dioxiranes: a half-century journey

El‐Assaad¹,

Zhu²,

Sebastian³

et al. 2022

Org. Chem. Front.

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Section: Mcgrath'smentioning

confidence: 99%

Section: Generation Isolation and Characterization Of Dioxiranesmentioning

confidence: 99%

Dioxiranes: a half-century journey

El‐Assaad¹,

Zhu²,

Sebastian³

et al. 2022

Org. Chem. Front.

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“…18 The use of organic oxidants in total synthesis was recently reviewed and will not be covered here. 19 Scheme 5 Key C-H oxidation by DMDO in the total synthesis of Taxol ® (9)…”

Section: Template For Synthesis Thiemementioning

confidence: 99%

“…18 The use of or-ganic oxidants in total synthesis was recently reviewed and will not be covered here. 19 The ubiquity of carbon and hydrogen in organic molecules and chemoselectivity issues through functional group intolerance impose site-and chemoselectivity challenges in the oxidation of C-H bonds in complex molecules. As a result, there is a limited number of examples of total syntheses using aliphatic C-H bond oxidations.…”

Section: Review Synthesismentioning

confidence: 99%

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Metal-Catalyzed C–H Bond Oxidation in the Total Synthesis of Natural and Unnatural Products

et al. 2022

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C―H bond oxidation has arisen as a powerful means for oxygen incorporation in organic molecules. Its use results in fast structural diversification and in a new way of thinking about retrosynthetic disconnections. In this review, we present the application of five metal-catalyzed methodologies for C(sp3)―H oxidation in the total synthesis of natural and unnatural products, covering the period of 2004–2022.

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Dioxirane‐Based Stereoselective and Oxidative Transformations

Neogi,

Parida

2024

ChemistrySelect

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The synthesis of chiral organic molecules is a purity‐driven research that has become an essential part of our lives due to their applications in pharmaceuticals. Contemporary research focuses on the exploration of synthetic protocols that obviate the use/generation of hazardous chemicals. In this regard, dioxiranes are readily accessed as a reagent solution or catalyst (in situ) from the reaction of ketone with a co‐oxidant like Oxone® or H2O2; the latter makes the protocol very green and inexpensive. It has shown the potential to replace transition metal‐based oxygenation protocols. The dioxirane‐mediated asymmetric reactions include oxidations, epoxidations, C−H hydroxylations, etc. Both stoichiometric and catalytic protocols of dioxiranes are been explored for the oxyfunctionalization of chiral natural product derivatives such as Penicillin, nucleosides, amino acids, carbohydrates, etc. In addition, these are employed as key oxygenation agents during the synthesis of natural products like (+)‐Plagiogyrin A, Portimine, Taxol, Bryostatin, dafachronic acid, majucinoids, eldecalcitol, Spirochensilide A, etc. The review consolidates the development of both achiral and chiral dioxiranes in application to asymmetric synthesis and oxygenation of chiral molecules.

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Oxidative Semisynthesis of Natural Products with DMDO

Cited by 5 publications

References 0 publications

Dioxiranes: a half-century journey

Dioxiranes: a half-century journey

Metal-Catalyzed C–H Bond Oxidation in the Total Synthesis of Natural and Unnatural Products

Dioxirane‐Based Stereoselective and Oxidative Transformations

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