Selective Synthesis of 5,6-Disubstituted 3-Methyl-2(2H)-pyranones and 6-Substituted 3-Methyl-2(2H)-pyranones, Including Fusalanipyrone and Gibepyrone A

Biagetti, Matteo; Bellina, Fabio; Carpita, Adriano; Viel, Stéphane; Mannina, Luisa; Rossi, Renzo

doi:10.1002/1099-0690(200203)2002:6<1063::aid-ejoc1063>3.0.co;2-m

Cited by 41 publications

(18 citation statements)

References 84 publications

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“…38) Consequently, the geometric configuration of the 2-butenyl group in nocapyrone H (1) was consistent with the E-configuration. Thus, the structure of 1 was determined to be (E)-6-(but-2-en-2-yl)-3-isobutyl-2H-pyran-2-one.…”

Section: Resultsmentioning

confidence: 99%

Nocapyrones H–J, 3,6-Disubstituted α-Pyrones from the Marine Actinomycete <i>Nocardiopsis</i> sp. KMF-001

et al. 2013

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Three new 3,6-disubstituted α-pyrones, nocapyrones H-J (1-3), were isolated from the marine actinomycete Nocardiopsis sp. KMF-001. Their structures were assigned to be 3-alkylated 6-(1-methyl-1-propenyl)-2H-pyran-2-ones on the basis of UV, MS, NMR, and high resolution (HR)-FAB-MS analyses. Nocapyrone H (1) reduced the pro-inflammatory factor such as nitric oxide (NO), prostaglandin E 2 (PGE 2 ) and interleukin-1β (IL-1β). Moreover, nocapyrone H showed 5.82% stronger inhibitory effect on NO production than chrysin at a concentration of 10 µm in lipopolysaccharide (LPS)-stimulated BV-2 microglial cells.

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Section: Resultsmentioning

confidence: 99%

Nocapyrones H–J, 3,6-Disubstituted α-Pyrones from the Marine Actinomycete <i>Nocardiopsis</i> sp. KMF-001

et al. 2013

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“…1) supported the suggestion that the 2-buten-2-yl and isobutyl residues were linked to C-6 and C-3 of the 2-pyrone nucleus, respectively. 17,18 This deduction was conrmed from a NOE difference experiment. 13,16 By contrast, a related compound, fusalanipyrone with a Z-conguration, showed downeld shi of H 3 C-10 (d C 21.5).…”

Section: Resultsmentioning

confidence: 99%

α-Pyrones from the marine-derived actinomycete Nocardiopsis dassonvillei subsp. dassonvillei XG-8-1

Gong

et al. 2013

RSC Adv.

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Seven new a-pyrones, nocapyrones H-N (1-7) were isolated from the marine-derived actinomycete strain, Nocardiopsis dassonvillei subsp. dassonvillei XG-8-1. The new structures 1-7 were determined by spectroscopic analysis, CD spectra, ECD quantum chemical calculations and the modified Mosher's method. Compounds 1, 2 and 6 showed inhibitory effects on quorum sensing (QS) controlled gene expression in Chromobacterium violaceum CV026 and Pseudomonas aeruginosa QSIS-lasI biosensors at a concentration of 100 mg mL À1 , respectively. This is the first report of inhibition of a-pyrones on QS controlled gene expression in pathogenic bacteria. † Electronic supplementary information (ESI) available: Bioassay protocols used, 16S rRNA gene sequences of Nocardiopsis dassonvillei subsp. dassonvillei XG-8-1, the NMR spectra of compounds 1-7. See

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“…It was observed that alcohols led to trans products in low selectivity, while ethers and silylethers produced cis isomers in excellent selectivity ( Table 2). A possible explanation for this high selectivity is the greater stability (due to the lack of vicinal interaction) of the oxonium ion intermediate (12) compared to (13) and (14), where R 1 is a bulk group (in the case of ethers and silylethers).…”

Section: Intramolecular Coiodination Of Alkenols and Unsaturated Ethementioning

confidence: 99%

A Centennial Methodology for the Preparation of Heterocyclic Compounds: The Intramolecular Coiodination of Alkenes with Internal Oxygenated Nucleophiles

Silva¹,

Jones²,

Mattos³

2005

COS

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A review on the intramolecular coiodination of alkenes with internal oxygenated nucleophiles (alkenols, unsaturated ethers, carboxylic acids and derivatives) is presented. The reactions are discussed with emphasis in the preparation of iodotetrahydrofurans, iodotetrahydropyrans and iodolactones and their utilization in organic synthesis. The intramolecular coiodination of alkenes with less common oxygenated nucleophiles (unsaturated carbonates, phosphates, isoxazolines, uretanes, hydroperoxides and silenols) is also presented. da Silva et al.Recently, we reported the intermolecular coiodination of alkenes with oxygenated nucleophiles [17], and the products (iodohydrins, β-iodoethers and β-iodoesters) proved to be

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Selective Synthesis of 5,6-Disubstituted 3-Methyl-2(2H)-pyranones and 6-Substituted 3-Methyl-2(2H)-pyranones, Including Fusalanipyrone and Gibepyrone A

Cited by 41 publications

References 84 publications

Nocapyrones H–J, 3,6-Disubstituted α-Pyrones from the Marine Actinomycete <i>Nocardiopsis</i> sp. KMF-001

Nocapyrones H–J, 3,6-Disubstituted α-Pyrones from the Marine Actinomycete <i>Nocardiopsis</i> sp. KMF-001

α-Pyrones from the marine-derived actinomycete Nocardiopsis dassonvillei subsp. dassonvillei XG-8-1

A Centennial Methodology for the Preparation of Heterocyclic Compounds: The Intramolecular Coiodination of Alkenes with Internal Oxygenated Nucleophiles

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