Diversity oriented microwave-assisted synthesis of (-)-steganacin aza-analogues / Mont N., Mehta V.P., Appukkuttan P., Beryozkina T., Toppet S., Van Hecke K., Van Meervelt L., Voet A., DeMaeyer M., Van Der Eycken E. // Journal of Organic Chemistry. - 2008. - V. 73, l. 19. - P. 7509-7516.

ISSN:

00223263

Type:

Article

Abstract:

(Chemical Equation Presented) 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 A3-coupling, as well as the intramolecular Huisgen 1,3-dipolar cycloaddition. © 2008 American Chemical Society.

Author keywords:

Index keywords:

Chemical equations; Focused microwave; Highly efficient; Inhibitory activities; Microwave-assisted synthesis; Ring closures; Suzuki-Miyaura reactions; Synthesis of; TO effect; Tubulin polymerization;

DOI:

10.1021/jo801290j

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https://www.scopus.com/inward/record.uri?eid=2-s2.0-53149142153&doi=10.1021%2fjo801290j&partnerID=40&md5=3150bce192ee8c8823b7a5b06f0cf0f6

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Affiliations	Laboratory for Organic and Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, Katholieke Universiteit Leuven, Celestijnenlaan 200F, B-3001, Heverlee, Leuven, Belgium; Department of Chemistry, Katholieke Universiteit Leuven, Celestijnenlaan 200F, B-3001, Heverlee (Leuven), Belgium; Biomolecular Architecture, Department of Chemistry, Katholieke Universiteit Leuven, Celestijnenlaan 200F, B-3001, Heverlee (Leuven), Belgium; Molecular and Structural Biology, Katholieke Universiteit Leuven, Celestijnenlaan 200D, B-3001 Heverlee (Leuven), Belgium; Prous Institute for Biomedical Research, Roger de Lluria, 118, 3-2, 08037 Barcelona, Spain; Department of Chemistry, Ludwig-Maximilians-Universität, Building F, Butenandtstrasse 5-13, D-81377 Munich, Germany; Organic Chemistry Department, V.N. Karazin Kharkiv National University, Svoboda sq. 4, 61077 Kharkiv, Ukraine
Chemicals/CAS	copper, 15158-11-9, 7440-50-8; steganacin, 41451-68-7; 4-Butyrolactone, 96-48-0; Antineoplastic Agents; Aza Compounds; Lactones; Lignans; Tubulin Modulators; steganacin, 41451-68-7
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Correspondence Address	Van Der Eycken, E.; Laboratory for Organic and Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, Katholieke Universiteit Leuven, Celestijnenlaan 200F, B-3001, Heverlee, Leuven, Belgium; email: erik.vandereycken@chem.kuleuven.be
CODEN	JOCEA
PubMed ID	18754579
Language of Original Document	English
Abbreviated Source Title	J. Org. Chem.
Source	Scopus