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

(2008) JOURNAL OF ORGANIC CHEMISTRY. 73(19). p.7509-7516
Author
Organization
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.
Keywords
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

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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.
@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},
}

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