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A three-step synthesis of the guaianolide ring system

Jan Hullaert (UGent), Duchan Laplace and Johan Winne (UGent)
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Abstract
By using a gallium(III) triflate catalyzed intramolecular (4+3) cycloaddition, a few functionalized furan-derived tricycles that share the common guaianolide sesquiterpene ring system were prepared in a stereoselective manner in only three steps from commercially available starting materials. A discussion of the formation of alternative products is included, with possible substrate requirements to achieve the key cycloaddition step in an efficient way.
Keywords
Cycloaddition, INTRAMOLECULAR 4+3 CYCLOADDITIONS, Oxygen heterocycles, Terpenoids, Natural products, Total synthesis, DIVERSITY-ORIENTED SYNTHESIS, SESQUITERPENE LACTONES, BIOSYNTHESIS, (&/-)-ESTAFIATIN, SKELETON, CATIONS, ACCESS, AGENTS, ROUTE

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Citation

Please use this url to cite or link to this publication:

Chicago
Hullaert, Jan, Duchan Laplace, and Johan Winne. 2014. “A Three-step Synthesis of the Guaianolide Ring System.” European Journal of Organic Chemistry (15): 3097–3100.
APA
Hullaert, J., Laplace, D., & Winne, J. (2014). A three-step synthesis of the guaianolide ring system. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, (15), 3097–3100.
Vancouver
1.
Hullaert J, Laplace D, Winne J. A three-step synthesis of the guaianolide ring system. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. 2014;(15):3097–100.
MLA
Hullaert, Jan, Duchan Laplace, and Johan Winne. “A Three-step Synthesis of the Guaianolide Ring System.” EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 15 (2014): 3097–3100. Print.
@article{4378443,
  abstract     = {By using a gallium(III) triflate catalyzed intramolecular (4+3) cycloaddition, a few functionalized furan-derived tricycles that share the common guaianolide sesquiterpene ring system were prepared in a stereoselective manner in only three steps from commercially available starting materials. A discussion of the formation of alternative products is included, with possible substrate requirements to achieve the key cycloaddition step in an efficient way.},
  author       = {Hullaert, Jan and Laplace, Duchan and Winne, Johan},
  issn         = {1434-193X},
  journal      = {EUROPEAN JOURNAL OF ORGANIC CHEMISTRY},
  keyword      = {Cycloaddition,INTRAMOLECULAR 4+3 CYCLOADDITIONS,Oxygen heterocycles,Terpenoids,Natural products,Total synthesis,DIVERSITY-ORIENTED SYNTHESIS,SESQUITERPENE LACTONES,BIOSYNTHESIS,(\&/-)-ESTAFIATIN,SKELETON,CATIONS,ACCESS,AGENTS,ROUTE},
  language     = {eng},
  number       = {15},
  pages        = {3097--3100},
  title        = {A three-step synthesis of the guaianolide ring system},
  url          = {http://dx.doi.org/10.1002/ejoc.201402170},
  year         = {2014},
}

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