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Diversity oriented microwave-assisted synthesis of (-)-Steganacin aza-analogues

Nuria Mont, Vaibhav Pravinchandra Mehta, Prasad Appukkuttan, Tetyana Beryozkina, Suzzane Toppet, Kristof Van Hecke UGent, Luc Van Meervelt, Arnout Voet, Marc DeMaeyer and Erik Van der Eycken (2008) JOURNAL OF ORGANIC CHEMISTRY. 73(19). p.7509-7516
abstract
A novel microwave-assisted, highly efficient protocol for the synthesis of hitherto unknown aza-analogues of (-)-Steganacin, a naturally occurring bisbenzocyclooctadiene lignan lactone with potent antileukemic and tubulin polymerization inhibitory activity, has been developed. Focused microwave irradiation is demonstrated to be highly beneficial in promoting the three crucial steps of the sequence to effect the final ring closure: the Suzuki-Miyaura reaction, Cu-mediated A(3)-coupling, as well as the intramolecular Huisgen 1,3-dipolar cycloaddition.
Please use this url to cite or link to this publication:
author
organization
year
type
journalArticle (original)
publication status
published
subject
keyword
C-H ACTIVATION, ASYMMETRIC TOTAL-SYNTHESIS, HIGHLY ENANTIOSELECTIVE SYNTHESIS, CROSS-COUPLING REACTIONS, ALDEHYDE-ALKYNE-AMINE, FLUORO ACID-MEDIUM, CLICK CHEMISTRY, TERMINAL ALKYNES, FORMAL SYNTHESIS, NICKEL(0)-CATALYZED <2+2+2>-COCYCLIZATION
journal title
JOURNAL OF ORGANIC CHEMISTRY
J. Org. Chem.
volume
73
issue
19
pages
7509 - 7516
Web of Science type
Article
Web of Science id
000259574700010
JCR category
CHEMISTRY, ORGANIC
JCR impact factor
3.952 (2008)
JCR rank
7/55 (2008)
JCR quartile
1 (2008)
ISSN
0022-3263
DOI
10.1021/jo801290j
language
English
UGent publication?
no
classification
A1
id
2045776
handle
http://hdl.handle.net/1854/LU-2045776
date created
2012-02-27 11:02:18
date last changed
2018-01-29 12:12:31
@article{2045776,
  abstract     = {A novel microwave-assisted, highly efficient protocol for the synthesis of hitherto unknown aza-analogues of (-)-Steganacin, a naturally occurring bisbenzocyclooctadiene lignan lactone with potent antileukemic and tubulin polymerization inhibitory activity, has been developed. Focused microwave irradiation is demonstrated to be highly beneficial in promoting the three crucial steps of the sequence to effect the final ring closure: the Suzuki-Miyaura reaction, Cu-mediated A(3)-coupling, as well as the intramolecular Huisgen 1,3-dipolar cycloaddition.},
  author       = {Mont, Nuria and Mehta, Vaibhav Pravinchandra and Appukkuttan, Prasad and Beryozkina, Tetyana and Toppet, Suzzane and Van Hecke, Kristof and Van Meervelt, Luc and Voet, Arnout and DeMaeyer, Marc and Van der Eycken, Erik},
  issn         = {0022-3263},
  journal      = {JOURNAL OF ORGANIC CHEMISTRY},
  keyword      = {C-H ACTIVATION,ASYMMETRIC TOTAL-SYNTHESIS,HIGHLY ENANTIOSELECTIVE SYNTHESIS,CROSS-COUPLING REACTIONS,ALDEHYDE-ALKYNE-AMINE,FLUORO ACID-MEDIUM,CLICK CHEMISTRY,TERMINAL ALKYNES,FORMAL SYNTHESIS,NICKEL(0)-CATALYZED {\textlangle}2+2+2{\textrangle}-COCYCLIZATION},
  language     = {eng},
  number       = {19},
  pages        = {7509--7516},
  title        = {Diversity oriented microwave-assisted synthesis of (-)-Steganacin aza-analogues},
  url          = {http://dx.doi.org/10.1021/jo801290j},
  volume       = {73},
  year         = {2008},
}

Chicago
Mont, Nuria, Vaibhav Pravinchandra Mehta, Prasad Appukkuttan, Tetyana Beryozkina, Suzzane Toppet, Kristof Van Hecke, Luc Van Meervelt, Arnout Voet, Marc DeMaeyer, and Erik Van der Eycken. 2008. “Diversity Oriented Microwave-assisted Synthesis of (-)-Steganacin Aza-analogues.” Journal of Organic Chemistry 73 (19): 7509–7516.
APA
Mont, N., Mehta, V. P., Appukkuttan, P., Beryozkina, T., Toppet, S., Van Hecke, K., Van Meervelt, L., et al. (2008). Diversity oriented microwave-assisted synthesis of (-)-Steganacin aza-analogues. JOURNAL OF ORGANIC CHEMISTRY, 73(19), 7509–7516.
Vancouver
1.
Mont N, Mehta VP, Appukkuttan P, Beryozkina T, Toppet S, Van Hecke K, et al. Diversity oriented microwave-assisted synthesis of (-)-Steganacin aza-analogues. JOURNAL OF ORGANIC CHEMISTRY. 2008;73(19):7509–16.
MLA
Mont, Nuria, Vaibhav Pravinchandra Mehta, Prasad Appukkuttan, et al. “Diversity Oriented Microwave-assisted Synthesis of (-)-Steganacin Aza-analogues.” JOURNAL OF ORGANIC CHEMISTRY 73.19 (2008): 7509–7516. Print.