Publikation:

Synthetic Efforts Towards the Synthesis of the Complex Diterpene Providencin

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2009

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Weinstabl, Harald
Mulzer, Johann

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https://doi.org/10.1055/s-0028-1216728
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Published

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Synlett. 2009, 2009(09), pp. 1357-1366. ISSN 0936-5214. eISSN 1437-2096. Available under: doi: 10.1055/s-0028-1216728

Zusammenfassung

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.

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Fachgebiet (DDC)
540 Chemie

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furanocembranolides, total synthesis, macrocycles, Horner-­Wadsworth-Emmons olefination, ring-closing metathesis

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ISO 690GAICH, 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
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}
}
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