1. Diversity oriented microwave-assisted synthesis of (-)-steganacin aza-analogues.
- Author
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Mont N, Mehta VP, Appukkuttan P, Beryozkina T, Toppet S, Van Hecke K, Van Meervelt L, Voet A, DeMaeyer M, and Van der Eycken E
- Subjects
- 4-Butyrolactone chemical synthesis, Antineoplastic Agents chemical synthesis, Lactones, Microwaves, Tubulin Modulators chemical synthesis, 4-Butyrolactone analogs & derivatives, Aza Compounds chemical synthesis, Lignans chemical synthesis
- 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 A3-coupling, as well as the intramolecular Huisgen 1,3-dipolar cycloaddition.
- Published
- 2008
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