Synthetic Efforts Towards the Synthesis of the Complex Diterpene Providencin
| dc.contributor.author | Gaich, Tanja | |
| dc.contributor.author | Weinstabl, Harald | |
| dc.contributor.author | Mulzer, Johann | |
| dc.date.accessioned | 2017-11-16T14:45:18Z | |
| dc.date.available | 2017-11-16T14:45:18Z | |
| dc.date.issued | 2009-06 | eng |
| dc.description.abstract | Providencin is a novel, highly oxygenated marine furanocembranolide featuring a cyclobutane ring and a highly strained 7,8-trans-epoxide. Various approaches to the total synthesis of this compound are reported. The cyclobutane moiety is generated via [2+2] cycloaddition and the furan ring is constructed via a Wipf palladium-catalyzed alkynone cyclization. The macrocyclic ring is closed via a Horner-Wadsworth-Emmons olefination or ring-closing metathesis. The latter reaction, however, produces the undesired 7,8-Z-olefin exclusively, and the conversion into the E-isomer has been, thus far, unsuccessful. | eng |
| dc.description.version | published | eng |
| dc.identifier.doi | 10.1055/s-0028-1216728 | eng |
| dc.identifier.uri | https://kops.uni-konstanz.de/handle/123456789/40652 | |
| dc.language.iso | eng | eng |
| dc.subject | furanocembranolides, total synthesis, macrocycles, Horner-Wadsworth-Emmons olefination, ring-closing metathesis | eng |
| dc.subject.ddc | 540 | eng |
| dc.title | Synthetic Efforts Towards the Synthesis of the Complex Diterpene Providencin | eng |
| dc.type | JOURNAL_ARTICLE | eng |
| dspace.entity.type | Publication | |
| kops.citation.bibtex | @article{Gaich2009-06Synth-40652,
year={2009},
doi={10.1055/s-0028-1216728},
title={Synthetic Efforts Towards the Synthesis of the Complex Diterpene Providencin},
number={09},
volume={2009},
issn={0936-5214},
journal={Synlett},
pages={1357--1366},
author={Gaich, Tanja and Weinstabl, Harald and Mulzer, Johann}
} | |
| kops.citation.iso690 | GAICH, Tanja, Harald WEINSTABL, Johann MULZER, 2009. Synthetic Efforts Towards the Synthesis of the Complex Diterpene Providencin. In: Synlett. 2009, 2009(09), pp. 1357-1366. ISSN 0936-5214. eISSN 1437-2096. Available under: doi: 10.1055/s-0028-1216728 | deu |
| kops.citation.iso690 | GAICH, Tanja, Harald WEINSTABL, Johann MULZER, 2009. Synthetic Efforts Towards the Synthesis of the Complex Diterpene Providencin. In: Synlett. 2009, 2009(09), pp. 1357-1366. ISSN 0936-5214. eISSN 1437-2096. Available under: doi: 10.1055/s-0028-1216728 | eng |
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<dcterms:abstract xml:lang="eng">Providencin is a novel, highly oxygenated marine furanocembranolide featuring a cyclobutane ring and a highly strained 7,8-trans-epoxide. Various approaches to the total synthesis of this compound are reported. The cyclobutane moiety is generated via [2+2] cycloaddition and the furan ring is constructed via a Wipf palladium-catalyzed alkynone cyclization. The macrocyclic ring is closed via a Horner-Wadsworth-Emmons olefination or ring-closing metathesis. The latter reaction, however, produces the undesired 7,8-Z-olefin exclusively, and the conversion into the E-isomer has been, thus far, unsuccessful.</dcterms:abstract>
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| kops.sourcefield | Synlett. 2009, <b>2009</b>(09), pp. 1357-1366. ISSN 0936-5214. eISSN 1437-2096. Available under: doi: 10.1055/s-0028-1216728 | deu |
| kops.sourcefield.plain | Synlett. 2009, 2009(09), pp. 1357-1366. ISSN 0936-5214. eISSN 1437-2096. Available under: doi: 10.1055/s-0028-1216728 | deu |
| kops.sourcefield.plain | Synlett. 2009, 2009(09), pp. 1357-1366. ISSN 0936-5214. eISSN 1437-2096. Available under: doi: 10.1055/s-0028-1216728 | eng |
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