Photosensitised oxidation of 3β-acetoxylanost-8-ene

Fox, J. E.; Scott, A. I.; Young, Douglas W.

doi:10.1039/c19670001105

Chem. Commun. (London)

1967

DOI: 10.1039/c19670001105

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Photosensitised oxidation of 3β-acetoxylanost-8-ene

J. E. Fox¹,

A. I. Scott²,

Douglas W. Young³

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1978

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Cited by 4 publications

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“…18 More recently, a structurally related ergostane-derived 8,9-epoxy-8,9-secosteroid has been obtained from a higher basidiomycete fungus, Tylopilus plumbeoviolaceus. 21 Interestingly, during early photooxygenation studies of 3β-acetoxylanost-8-ene, among other products, the Criegee rearrangement product 3β-acetoxy-8,9-epoxy-8,9-secolanosta-7,9(11)-diene has been synthesized, 22 but the reaction conditions applied (reaction conducted in pyridine in the presence of p-nitrobenzenesulfonyl chloride and hematoporphyrin) were probably too harsh to consider the above mentioned natural products as simple oxidation artifacts of corresponding unsaturated steroid precursors with intact carbon skeletons. When tested for biological activity, eryloside A (1) displayed mild antibiotic and antifungal activity against E. coli, B. subtilis, and C. albicans.…”

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confidence: 99%

New steroidal saponins from the sponge Erylus lendenfeldi

Fouad¹,

Al-Trabeen²,

Badran³

et al. 2004

Arkivoc

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Our search for biologically active marine natural products has led to the isolation of two new steroidal saponins, eryloside K (2) and eryloside L (3) together with the known antitumor and antifungal glycoside eryloside A (1) from the organic extract of the sponge Erylus lendenfeldi (Geodiidae) collected in the Red Sea. The structures of the new compounds were elucidated on the basis of comprehensive spectral analyses ( 1 H, 13 C, COSY, HMQC, HMBC and TOCSY NMR) as well as GC/MS analysis to infer the absolute stereochemistry of the sugar moieties. Eryloside K (2) is the 24,25-didehydro congener of 1, while eryloside L (3) features an unusual 8α,9α-epoxy-4α-methyl-8,9-secocholesta-7,9(11),14-triene skeleton which appears to be unprecedented in nature. Eryloside A (1) displayed antibacterial activity against Bacillus subtilis and Escherichia coli together with antifungal activity against Candida albicans.

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mentioning

confidence: 99%

New steroidal saponins from the sponge Erylus lendenfeldi

Fouad¹,

Al-Trabeen²,

Badran³

et al. 2004

Arkivoc

View full text Add to dashboard Cite

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Green and Efficient: Iron-Catalyzed Selective Oxidation of Olefins to Carbonyls with O₂

2015

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A mild and operationally simple iron-catalyzed protocol for the selective aerobic oxidation of aromatic olefins to carbonyl compounds is described. Catalyzed by a Fe(III) species bearing a pyridine bisimidazoline ligand at 1 atm of O2, α- and β-substituted styrenes were cleaved to afford benzaldehydes and aromatic ketones generally in high yields with excellent chemoselectivity and very good functional group tolerance, including those containing radical-sensitive groups. With α-halo-substituted styrenes, the oxidation took place with concomitant halide migration to afford α-halo acetophenones. Various observations have been made, pointing to a mechanism in which both molecular oxygen and the olefinic substrate coordinate to the iron center, leading to the formation of a dioxetane intermediate, which collapses to give the carbonyl product.

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Sterol Metabolism. Xlii. On the Interception of Singlet Molecular Oxygen by Sterols

Smith¹,

Stroud²

1978

Photochem & Photobiology

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Abstract— The use of cyclic 1,3‐dienes and polycyclic aromatic hydrocarbons as xenobiotic substrates for the interception of electronically excited (singlet) molecular oxygen (1O2) in biological systems is reviewed and criticized, and the possibility of utilization of reactive endogenous substrates for 1O2 interception is considered. The common sterols, cholesterol, 5α‐cholest‐7‐en‐3β‐ol, and 5α‐lanost‐8‐en‐3β‐ol each give oxidation products with 1O2 different from those with ground‐state molecular oxygen that can be distinguished from one another by simple chromatographic means.

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Photosensitised oxidation of 3β-acetoxylanost-8-ene

Cited by 4 publications

References 0 publications

New steroidal saponins from the sponge Erylus lendenfeldi

New steroidal saponins from the sponge Erylus lendenfeldi

Green and Efficient: Iron-Catalyzed Selective Oxidation of Olefins to Carbonyls with O₂

Sterol Metabolism. Xlii. On the Interception of Singlet Molecular Oxygen by Sterols

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Photosensitised oxidation of 3β-acetoxylanost-8-ene

Cited by 4 publications

References 0 publications

New steroidal saponins from the sponge Erylus lendenfeldi

New steroidal saponins from the sponge Erylus lendenfeldi

Green and Efficient: Iron-Catalyzed Selective Oxidation of Olefins to Carbonyls with O2

Sterol Metabolism. Xlii. On the Interception of Singlet Molecular Oxygen by Sterols

Contact Info

Product

Resources

About

Green and Efficient: Iron-Catalyzed Selective Oxidation of Olefins to Carbonyls with O₂