Total synthesis of maesanin and analogues

Poigny, Stéphane; Guyot, Michèle; Samadi, Mohammad

doi:10.1016/s0040-4020(98)00927-2

Cited by 34 publications

(38 citation statements)

References 13 publications

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“…In 1992, Yadav et al reported a practical route for preparing 299 from 3-bromo-4-hydroxy-5-methoxybenzaldehyde [214] . Later, two synthetic routes for the preparation of 299 were reported by Poigny et al and Pfeifer et al, respectively [215,216] . A naphthoquinone derivative, cyclonoside A 303, was isolated from the leaves of the plant C paliurus.…”

Section: Wwwchinapharcom Jiang Cs Et Almentioning

confidence: 99%

Natural products possessing protein tyrosine phosphatase 1B (PTP1B) inhibitory activity found in the last decades

2012

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This article provides an overview of approximately 300 secondary metabolites with inhibitory activity against protein tyrosine phosphatase 1B (PTP1B), which were isolated from various natural sources or derived from synthetic process in the last decades. The structure-activity relationship and the selectivity of some compounds against other protein phosphatases were also discussed. Potential pharmaceutical applications of several PTP1B inhibitors were presented.

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Section: Wwwchinapharcom Jiang Cs Et Almentioning

confidence: 99%

Natural products possessing protein tyrosine phosphatase 1B (PTP1B) inhibitory activity found in the last decades

2012

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“…Samadi and co-workers suggested a most simple and effective approach for the synthesis of naturally occurring maesanin (14), and analogues [15]. 1,2,4,5-Tetramethoxybenzene is subjected to alkylation with BuLi and the appropriate alkyl bromide, and the resulting derivative, 11, is oxidatively demethyated by cerium(IV) ammonium nitrate (CAN) to a mixture of dimethoxy ortho-and paraquinones.…”

Section: Methodsmentioning

confidence: 99%

“…An analogous methodology was used by the same authors [16] for the synthesis of the marine natural product (-)-illimaquinone (15), which exhibits most interesting biological activity. The 6-methoxy isomer of ilimaquinone, 16, also formed, and was easily separated chromatographically.…”

Section: Methodsmentioning

confidence: 99%

Hydroxyquinones: Synthesis and Reactivity

Spyroudis

2000

Molecules

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“…After successfully alkylating 1,2,4,5-tetramethoxybenzene [2441- , the precursors to several naturally occurring quinones were oxidized with ceric ammonium nitrate (eq. 130) (186 …”

Section: ð36þmentioning

confidence: 99%

Quinones

Finley

2016

Kirk-Othmer Encyclopedia of Chemical Technology

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Quinones, possessing two α,β‐unsaturated carbonyl groups usually in a six‐carbon atom ring, represent a unique structural unit. Their centrality in the synthesis of such important commercial substances as dyes and pharmaceuticals has resulted in extensive studies. In living matter, they are ubiquitous and vital to human metabolism. Quinones are of special interest to biochemists and to both synthetic and theoretical organic chemists. The types of reactions most often reported are nucleophilic addition, photochemistry, cycloaddition, electrophilic addition, radical alkylation, electrochemical, oxidation, and nucleophilic substitution. The synthesis of quinones is usually accomplished through oxidation of phenols or anilines.

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Total synthesis of maesanin and analogues

Cited by 34 publications

References 13 publications

Natural products possessing protein tyrosine phosphatase 1B (PTP1B) inhibitory activity found in the last decades

Natural products possessing protein tyrosine phosphatase 1B (PTP1B) inhibitory activity found in the last decades

Hydroxyquinones: Synthesis and Reactivity

Quinones

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