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Data from: Bromonium Ion Induced Transannular Oxonium Ion...
- acs.figshare.com
txtUpdated May 31, 2023
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EmailClick to copy linkLink copiedCiteD. Christopher Braddock; David S. Millan; Yolanda Pérez-Fuertes; Rebecca H. Pouwer; Richard N. Sheppard; Savade Solanki; Andrew J. P. White (2023). Bromonium Ion Induced Transannular Oxonium Ion Formation−Fragmentation in Model Obtusallene Systems and Structural Reassignment of Obtusallenes V−VII [Dataset]. http://doi.org/10.1021/jo8026577.s002txtAvailable download formatsUnique identifierhttps://doi.org/10.1021/jo8026577.s002Dataset updatedMay 31, 2023Dataset provided byACS PublicationsAuthorsD. Christopher Braddock; David S. Millan; Yolanda Pérez-Fuertes; Rebecca H. Pouwer; Richard N. Sheppard; Savade Solanki; Andrew J. P. WhiteLicenseAttribution-NonCommercial 4.0 (CC BY-NC 4.0)https://creativecommons.org/licenses/by-nc/4.0/
License information was derived automaticallyDescriptionRing-closing metathesis was used to construct the strained 11-membered ring of obtusallenes II (and IV). Bromonium ion induced transannular oxonium ion formation−fragmentation gave the macrocyclic carbon skeleton of obtusallene VII with a bromine atom at C-13, in line with a previously published hypothesis. An additional brominated [5.5.1]bicyclotridecane adduct that must arise from a bromonium ion induced transannular oxonium ion formation−fragmentation could also be isolated, suggesting that this adduct represents the core of an as yet undiscovered natural product. An authentic sample of obtusallene V was studied by NMR spectroscopy, and the position of the halogens at C-7 and C-13 was reassigned on the basis of a 13C NMR chlorine induced isotopic shift. This revised structure was subsequently confirmed by X-ray crystallography. These findings allow us to confidently conclude that the structures of obtusallenes VII and VI should also be reassigned.
- n
10-Bromo-obtusallene
- coconut.naturalproducts.net
Updated May 17, 2024ShareFacebookTwitterEmailClick to copy linkLink copiedCiteCOCONUT - COlleCtion of Open Natural prodUcTs (2024). 10-Bromo-obtusallene [Dataset]. https://coconut.naturalproducts.net/compounds/CNP0122983.1Dataset updatedMay 17, 2024Dataset authored and provided byCOCONUT - COlleCtion of Open Natural prodUcTsLicenseAttribution 4.0 (CC BY 4.0)https://creativecommons.org/licenses/by/4.0/
License information was derived automaticallyDescriptionNatural product in the COCONUT database with details of source organisms, geolocations and citations.
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Data from: Structural Reassignment of Obtusallenes V, VI, and VII by...
- acs.figshare.com
- figshare.com
xlsUpdated May 30, 2023ShareFacebookTwitterEmailClick to copy linkLink copiedCiteD. Christopher Braddock; Henry S. Rzepa (2023). Structural Reassignment of Obtusallenes V, VI, and VII by GIAO-Based Density Functional Prediction [Dataset]. http://doi.org/10.1021/np0705918.s003xlsAvailable download formatsUnique identifierhttps://doi.org/10.1021/np0705918.s003Dataset updatedMay 30, 2023Dataset provided byACS PublicationsAuthorsD. Christopher Braddock; Henry S. RzepaLicenseAttribution-NonCommercial 4.0 (CC BY-NC 4.0)https://creativecommons.org/licenses/by-nc/4.0/
License information was derived automaticallyDescriptionRevised structures proposed previously for obtusallenes V−VII (5–7) have been confirmed on the basis of computed GIAO-DFT 13C NMR chemical shifts.
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Obtusallene IV
- coconut.naturalproducts.net
Updated May 16, 2024ShareFacebookTwitterEmailClick to copy linkLink copiedCiteCOCONUT - COlleCtion of Open Natural prodUcTs (2024). Obtusallene IV [Dataset]. https://coconut.naturalproducts.net/compounds/CNP0128726.1Dataset updatedMay 16, 2024Dataset authored and provided byCOCONUT - COlleCtion of Open Natural prodUcTsLicenseAttribution 4.0 (CC BY 4.0)https://creativecommons.org/licenses/by/4.0/
License information was derived automaticallyDescriptionNatural product in the COCONUT database with details of source organisms, geolocations and citations.
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Additional Insights into the Obtusallene Family: Components of Laurencia...
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txtUpdated Jun 1, 2023ShareFacebookTwitterEmailClick to copy linkLink copiedCiteAdrián Gutiérrez-Cepeda; José J. Fernández; Manuel Norte; Matías López-Rodríguez; Iván Brito; Christian D. Muller; María L. Souto (2023). Additional Insights into the Obtusallene Family: Components of Laurencia marilzae [Dataset]. http://doi.org/10.1021/acs.jnatprod.5b01080.s002txtAvailable download formatsUnique identifierhttps://doi.org/10.1021/acs.jnatprod.5b01080.s002Dataset updatedJun 1, 2023Dataset provided byACS PublicationsAuthorsAdrián Gutiérrez-Cepeda; José J. Fernández; Manuel Norte; Matías López-Rodríguez; Iván Brito; Christian D. Muller; María L. SoutoLicenseAttribution-NonCommercial 4.0 (CC BY-NC 4.0)https://creativecommons.org/licenses/by-nc/4.0/
License information was derived automaticallyDescriptionThe obtusallenes are a significant subset of C15-halogenated acetogenins that incorporate 12-membered cyclic ethers. We have recently reported the isolation from Laurencia marilzae of 12-epoxyobtusallene IV (1) and its related α,β-unsaturated carboxylate ester (2), both of special biogenetic relevance. Here we describe the final step of our study, the isolation of three new analogues (3–5), among these, the first bromopropargylic derivative (3) of this class of macrocyclic C15-acetogenins. The structures were elucidated by analysis of NMR and X-ray data. 12-Epoxyobtusallene IV (1), its new isomer 4, and known obtusallene IV (6) were evaluated for their apoptosis-inducing activities in a human hepatocarcinoma cell line.
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(-)-(as,4R,7S,9R,10R,12R,13S,14R)-12-bromo-7-chloro-obtusallene III
- coconut.naturalproducts.net
Updated May 17, 2024ShareFacebookTwitterEmailClick to copy linkLink copiedCiteCOCONUT - COlleCtion of Open Natural prodUcTs (2024). (-)-(as,4R,7S,9R,10R,12R,13S,14R)-12-bromo-7-chloro-obtusallene III [Dataset]. https://coconut.naturalproducts.net/compounds/CNP0429139.1Dataset updatedMay 17, 2024Dataset authored and provided byCOCONUT - COlleCtion of Open Natural prodUcTsLicenseAttribution 4.0 (CC BY 4.0)https://creativecommons.org/licenses/by/4.0/
License information was derived automaticallyDescriptionNatural product in the COCONUT database with details of source organisms, geolocations and citations.
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FacebookTwitterEmailData from: Bromonium Ion Induced Transannular Oxonium Ion Formation−Fragmentation in Model Obtusallene Systems and Structural Reassignment of Obtusallenes V−VII
Attribution-NonCommercial 4.0 (CC BY-NC 4.0)https://creativecommons.org/licenses/by-nc/4.0/
License information was derived automatically
Ring-closing metathesis was used to construct the strained 11-membered ring of obtusallenes II (and IV). Bromonium ion induced transannular oxonium ion formation−fragmentation gave the macrocyclic carbon skeleton of obtusallene VII with a bromine atom at C-13, in line with a previously published hypothesis. An additional brominated [5.5.1]bicyclotridecane adduct that must arise from a bromonium ion induced transannular oxonium ion formation−fragmentation could also be isolated, suggesting that this adduct represents the core of an as yet undiscovered natural product. An authentic sample of obtusallene V was studied by NMR spectroscopy, and the position of the halogens at C-7 and C-13 was reassigned on the basis of a 13C NMR chlorine induced isotopic shift. This revised structure was subsequently confirmed by X-ray crystallography. These findings allow us to confidently conclude that the structures of obtusallenes VII and VI should also be reassigned.