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Search for "eunicellane" in Full Text gives 2 result(s) in Beilstein Journal of Organic Chemistry.

Computation-guided scaffold exploration of 2E,6E-1,10-trans/cis-eunicellanes

  • Zining Li,
  • Sana Jindani,
  • Volga Kojasoy,
  • Teresa Ortega,
  • Erin M. Marshall,
  • Khalil A. Abboud,
  • Sandra Loesgen,
  • Dean J. Tantillo and
  • Jeffrey D. Rudolf

Beilstein J. Org. Chem. 2024, 20, 1320–1326, doi:10.3762/bjoc.20.115

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  • ., Davis, CA 95616, USA Academy of Scientific and Innovative Research (AcSIR), Ghaziabad, 201002, India Whitney Laboratory for Marine Bioscience, University of Florida, 9505 N Ocean Shore Blvd., St. Augustine, FL 32080, USA 10.3762/bjoc.20.115 Abstract Eunicellane diterpenoids are a unique family of
  • -eunicellane skeletons, respectively. Although the structures of these diterpenes only differed in their configuration at a single position, C1, they displayed distinct chemical and thermal reactivities. Here, we used a combination of quantum chemical calculations and chemical transformations to probe their
  • intrinsic properties, which result in protonation-initiated cyclization, Cope rearrangement, and atropisomerism. Finally, we exploited the reactivity of the trans-eunicellane skeleton to generate a series of 6/6/6 gersemiane-type diterpenes via electrophilic cyclization. Keywords: atropisomer; Cope
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Published 07 Jun 2024

Synthesis of eunicellane-type bicycles embedding a 1,3-cyclohexadiene moiety

  • Alex Frichert,
  • Peter G. Jones and
  • Thomas Lindel

Beilstein J. Org. Chem. 2018, 14, 2461–2467, doi:10.3762/bjoc.14.222

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  • The first synthesis of diterpenoid eunicellane skeletons incorporating a 1,3-cyclohexadiene moiety is presented. Key step is a low-valent titanium-induced pinacol cyclization that proved to be perfectly diastereoselective. Determination of the relative configuration of the diol was aided by the
  • reduction of non-cyclizing cyclohexane systems that were synthesized from limonene oxide. The title compounds and their synthetic precursors are prone to aromatization on contact with air oxygen. Attempted synthesis of cyclohexene-containing eunicellane bicycles by elimination of water from tertiary alkynyl
  • carbinols afforded novel allene systems. Our study may be of help towards the total synthesis of solenopodin or klysimplexin derivatives. Keywords: conformational analysis; low valent titanium; marine natural products; pinacol coupling; ten-membered rings; Introduction Eunicellane-type diterpenoids share
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Published 20 Sep 2018
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