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Stereoselective and modular assembly method for heterocycle-fused daucane sesquiterpenoids

Mien Christiaens (UGent) , Jan Hullaert (UGent) , Kristof Van Hecke (UGent) , Duchan Laplace (UGent) and Johan Winne (UGent)
(2018) CHEMISTRY-A EUROPEAN JOURNAL. 24(52). p.13783-13787
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Abstract
A stereoselective synthetic method is reported for the molecular framework found in common daucane and isodaucane sesquiterpenoid natural products. The synthetic method constitutes a scalable, modular, and also asymmetric access to a complex natural product scaffold, wherein the substitution pattern and the stereochemistry can be adjusted simply by choosing different starting materials. The method allows the rapid introduction of diverse heterocyclic substructures such as (benzo)furans, (benzo)thiophenes, dithiins, thiazoles, and indoles, which actually also facilitate and direct the key intramolecular annulation step.
Keywords
carbocations, cycloadditions, heterocycles, natural products, terpenoids, INTRAMOLECULAR 4+3 CYCLOADDITION, FURANOXONIUM IONS, BIOSYNTHESIS SPECULATION, NATURAL-PRODUCTS, RING-SYSTEM, DERIVATIVES, CYCLIZATION, CHEMISTRY, STRATEGY, RAMESWARALIDE

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Citation

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Chicago
Christiaens, Mien, Jan Hullaert, Kristof Van Hecke, Duchan Laplace, and Johan Winne. 2018. “Stereoselective and Modular Assembly Method for Heterocycle-fused Daucane Sesquiterpenoids.” Chemistry-a European Journal 24 (52): 13783–13787.
APA
Christiaens, Mien, Hullaert, J., Van Hecke, K., Laplace, D., & Winne, J. (2018). Stereoselective and modular assembly method for heterocycle-fused daucane sesquiterpenoids. CHEMISTRY-A EUROPEAN JOURNAL, 24(52), 13783–13787.
Vancouver
1.
Christiaens M, Hullaert J, Van Hecke K, Laplace D, Winne J. Stereoselective and modular assembly method for heterocycle-fused daucane sesquiterpenoids. CHEMISTRY-A EUROPEAN JOURNAL. 2018;24(52):13783–7.
MLA
Christiaens, Mien et al. “Stereoselective and Modular Assembly Method for Heterocycle-fused Daucane Sesquiterpenoids.” CHEMISTRY-A EUROPEAN JOURNAL 24.52 (2018): 13783–13787. Print.
@article{8581219,
  abstract     = {A stereoselective synthetic method is reported for the molecular framework found in common daucane and isodaucane sesquiterpenoid natural products. The synthetic method constitutes a scalable, modular, and also asymmetric access to a complex natural product scaffold, wherein the substitution pattern and the stereochemistry can be adjusted simply by choosing different starting materials. The method allows the rapid introduction of diverse heterocyclic substructures such as (benzo)furans, (benzo)thiophenes, dithiins, thiazoles, and indoles, which actually also facilitate and direct the key intramolecular annulation step.},
  author       = {Christiaens, Mien and Hullaert, Jan and Van Hecke, Kristof and Laplace, Duchan and Winne, Johan},
  issn         = {0947-6539},
  journal      = {CHEMISTRY-A EUROPEAN JOURNAL},
  keywords     = {carbocations,cycloadditions,heterocycles,natural products,terpenoids,INTRAMOLECULAR 4+3 CYCLOADDITION,FURANOXONIUM IONS,BIOSYNTHESIS SPECULATION,NATURAL-PRODUCTS,RING-SYSTEM,DERIVATIVES,CYCLIZATION,CHEMISTRY,STRATEGY,RAMESWARALIDE},
  language     = {eng},
  number       = {52},
  pages        = {13783--13787},
  title        = {Stereoselective and modular assembly method for heterocycle-fused daucane sesquiterpenoids},
  url          = {http://dx.doi.org/10.1002/chem.201803248},
  volume       = {24},
  year         = {2018},
}

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