Stein, Andreas, Thomopoulou, Persefoni Hilken Nee, Schulte, Tim, Neudoerfl, Joerg, Breugst, Martin and Schmalz, Hans-Guenther ORCID: 0000-0003-0489-1827
(2021).
Some Surprising Transformations of Colchicone and Other Colchicine-Derived Tropolones.
Eur. J. Org. Chem., 2021 (46).
S. 6375 - 6383.
WEINHEIM:
WILEY-V C H VERLAG GMBH.
ISSN 1099-0690
Abstract
The alkaloid colchicine represents a prominent lead structure for the development of tubulin-binding chemotherapeutics. In the course of explorative research into semi-synthetic colchicinoids we stumbled upon a number of unexpected and mechanistically surprising transformations which reflect the very particular reactivity of the tropolone ether unit and its interplay with adjacent functional groups. Examples are the selective C-8-methylation of colchicone upon reaction with the Wittig reagent triphenylphosphonium methylide, the AlMe3-mediated isomerization of colchicone to a tetracyclic lactone, and the cyanide-induced reaction of the colchicol-derived mesylate to a rearranged and ring B-defunctionalized cyano-allo-colchicinoid. Finally, the fragmenting rearrangement of a tetracyclic colchicinoid with (BF3OEt2)-O-. in the presence of vinyl-MgBr afforded a tropolonyl difluoroborate under concomitant transfer of an O-methyl group from ring C to ring A.
Item Type: | Journal Article | ||||||||||||||||||||||||||||
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URN: | urn:nbn:de:hbz:38-566211 | ||||||||||||||||||||||||||||
DOI: | 10.1002/ejoc.202100999 | ||||||||||||||||||||||||||||
Journal or Publication Title: | Eur. J. Org. Chem. | ||||||||||||||||||||||||||||
Volume: | 2021 | ||||||||||||||||||||||||||||
Number: | 46 | ||||||||||||||||||||||||||||
Page Range: | S. 6375 - 6383 | ||||||||||||||||||||||||||||
Date: | 2021 | ||||||||||||||||||||||||||||
Publisher: | WILEY-V C H VERLAG GMBH | ||||||||||||||||||||||||||||
Place of Publication: | WEINHEIM | ||||||||||||||||||||||||||||
ISSN: | 1099-0690 | ||||||||||||||||||||||||||||
Language: | English | ||||||||||||||||||||||||||||
Faculty: | Unspecified | ||||||||||||||||||||||||||||
Divisions: | Unspecified | ||||||||||||||||||||||||||||
Subjects: | no entry | ||||||||||||||||||||||||||||
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URI: | http://kups.ub.uni-koeln.de/id/eprint/56621 |
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