Photochemical Transformations of Small Ring Carbonyl Compounds. VIII. Photorearrangements in the Cyclopentenone Oxide Series<sup>1,2</sup>

Padwa, Albert; Hartman, R. J.

doi:10.1021/ja00959a037

Cited by 24 publications

(4 citation statements)

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“…The main concern in the execution of this strategy is the generation of the species 153 for which both photochemical and chemical methods have been explored. 4-Pyrones 156 have been shown − to rearrange on irradiation to oxyallyl zwitterions of type 157 , which unfolds a variety of ground-state reactions to furnish products such as 158 and 159 through solvent trapping and rearrangement, depending upon experimental conditions, Scheme .…”

Section: [4 + 3]-cycloaddition Of Oxyallyl Zwitterionsmentioning

confidence: 99%

Progress in the Construction of Cyclooctanoid Systems: New Approaches and Applications to Natural Product Syntheses

1999

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Section: [4 + 3]-cycloaddition Of Oxyallyl Zwitterionsmentioning

confidence: 99%

Progress in the Construction of Cyclooctanoid Systems: New Approaches and Applications to Natural Product Syntheses

1999

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“…Photolysis of 3,4-diphenyl-4,5-epoxy-2-cyclopentene-1-one in anhydrous ether at 25 °C for 10 min with ultraviolet light of wavelength above 260 nm could afford 4,5-diphenyl-2-pyrone. Subsequently, a p -terphenyl was obtained after 18 h of ultraviolet irradiation, , which indicated that compound 2 could be the biosynthetic precursor of p -terphenyl analogues.…”

Section: Resultsmentioning

confidence: 99%

“…Peniterphenyl B (2) was obtained as a yellow oil, and its molecular formula of C 17 H 12 O 6 was determined by HRESIMS analysis, which suggested 12 degrees of unsaturation. The 1 H and 13 C NMR data (Table 1) of 2 exhibited the presence of eight aromatic/olefinic methines, nine nonprotonated sp 2 carbons including an ester carbonyl (δ C 168.8, C-2), and four hydroxy groups (δ H 9.17 Subsequently, a p-terphenyl was obtained after 18 h of ultraviolet irradiation, 16,17 which indicated that compound 2 could be the biosynthetic precursor of p-terphenyl analogues.…”

mentioning

confidence: 99%

p-Terphenyls as Anti-HSV-1/2 Agents from a Deep-Sea-Derived Penicillium sp.

Chen

Zhang

et al. 2021

J. Nat. Prod.

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Guided by Global Natural Products Social molecular networking, two p-terphenyl derivatives and one 4,5-diphenyl-2-pyrone analogue, peniterphenyls A–C (1–3), together with five known p-terphenyl derivatives (4–8) and sulochrin (9), were obtained from a deep-sea-derived Penicillium sp. SCSIO41030. Their structures were elucidated using extensive NMR spectroscopic and HRESIMS data and by comparing the information with literature data. Peniterphenyl B (2) represented the first reported natural product possessing a 4,5-diphenyl-substituted 2-pyrone derivative. The p-terphenyl derivatives displayed inhibitory activities against HSV-1/2 with EC50 values ranging from 1.4 ± 0.6 to 9.3 ± 3.7 μM in Vero cells, which showed that they possessed antiviral activities with low cytotoxicity, superior to the current clinical drug acyclovir (EC50 3.6 ± 0.7 μM). Peniterphenyl A (1) inhibited HSV-1/2 virus entry into cells and may block HSV-1/2 infection through direct interaction with virus envelope glycoprotein D to interfere with virus adsorption and membrane fusion, and thus differs from the nucleoside analogues such as acyclovir. Our study indicated peniterphenyl A (1) could be a promising lead compound against HSV-1/2.

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“…Extensive studies of the photochemistry of pyran-4-ones in recent years have elucidated a number of mechanistically complex and synthetically intriguing photorearrangements and trapping processes for these simple, heterocyclic reactants. Early observations identified dimerization and unimolecular rearrangement to pyran-2-ones or furfurals as common pathways. It was subsequently found that irradiation of pyran-4-ones 1 in polar, protic solvents led to solvent adducts (eq 1) .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Bridged Bicyclic Ethers and Fused Oxetanes from Pyran-4-ones via Tandem Solvent Trapping and Norrish Type II Cyclization¹

et al. 1999

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Polyalkyl pyran-4-ones 1a-c were irradiated in methanol or ethanol. Although the expected solvent trapping products 3 could be observed, extended irradiation times allowed exclusive formation of secondary photoproducts 4 and 5 in combined yields of 37-64%. These bicyclic compounds are believed to arise from gamma-hydrogen abstraction by the excited enone chromophore of 3, followed by closure of the resulting biradical through one of two possible pathways. Moderate stereoselectivity was observed in the radical coupling to produce 4, whereas the analogous closure to 5 was completely diastereoselective. Tautomerization of the enol precursors to 5 also occurred with complete selectivity for protonation from the exo face. Overall, this process converts simple, planar heterocycles and alkanols into complex products in a single transformation.

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Photochemical Transformations of Small Ring Carbonyl Compounds. VIII. Photorearrangements in the Cyclopentenone Oxide Series^1,2

Cited by 24 publications

References 0 publications

Progress in the Construction of Cyclooctanoid Systems: New Approaches and Applications to Natural Product Syntheses

Progress in the Construction of Cyclooctanoid Systems: New Approaches and Applications to Natural Product Syntheses

p-Terphenyls as Anti-HSV-1/2 Agents from a Deep-Sea-Derived Penicillium sp.

Synthesis of Bridged Bicyclic Ethers and Fused Oxetanes from Pyran-4-ones via Tandem Solvent Trapping and Norrish Type II Cyclization¹

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Photochemical Transformations of Small Ring Carbonyl Compounds. VIII. Photorearrangements in the Cyclopentenone Oxide Series1,2

Cited by 24 publications

References 0 publications

Progress in the Construction of Cyclooctanoid Systems: New Approaches and Applications to Natural Product Syntheses

Progress in the Construction of Cyclooctanoid Systems: New Approaches and Applications to Natural Product Syntheses

p-Terphenyls as Anti-HSV-1/2 Agents from a Deep-Sea-Derived Penicillium sp.

Synthesis of Bridged Bicyclic Ethers and Fused Oxetanes from Pyran-4-ones via Tandem Solvent Trapping and Norrish Type II Cyclization1

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Photochemical Transformations of Small Ring Carbonyl Compounds. VIII. Photorearrangements in the Cyclopentenone Oxide Series^1,2

Synthesis of Bridged Bicyclic Ethers and Fused Oxetanes from Pyran-4-ones via Tandem Solvent Trapping and Norrish Type II Cyclization¹