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A three-step synthesis of the guaianolide ring system

Jan Hullaert UGent, Duchan Laplace and Johan Winne UGent (2014) EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. p.3097-3100
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.
Please use this url to cite or link to this publication:
author
organization
year
type
journalArticle (original)
publication status
published
subject
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
journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Eur. J. Org. Chem.
issue
15
pages
3097 - 3100
Web of Science type
Article
Web of Science id
000336377000008
JCR category
CHEMISTRY, ORGANIC
JCR impact factor
3.065 (2014)
JCR rank
14/58 (2014)
JCR quartile
1 (2014)
ISSN
1434-193X
DOI
10.1002/ejoc.201402170
language
English
UGent publication?
yes
classification
A1
copyright statement
I have transferred the copyright for this publication to the publisher
id
4378443
handle
http://hdl.handle.net/1854/LU-4378443
date created
2014-05-07 09:45:50
date last changed
2016-12-19 15:46:07
@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},
}

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.