Universität zu Köln

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

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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
Creators:	Creators Email ORCID ORCID Put Code Stein, Andreas UNSPECIFIED UNSPECIFIED UNSPECIFIED Thomopoulou, Persefoni Hilken Nee UNSPECIFIED UNSPECIFIED UNSPECIFIED Schulte, Tim UNSPECIFIED UNSPECIFIED UNSPECIFIED Neudoerfl, Joerg UNSPECIFIED UNSPECIFIED UNSPECIFIED Breugst, Martin UNSPECIFIED UNSPECIFIED UNSPECIFIED Schmalz, Hans-Guenther UNSPECIFIED orcid.org/0000-0003-0489-1827 UNSPECIFIED
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
Uncontrolled Keywords:	Keywords Language BIOLOGICAL EVALUATION; ANALOGS; (-)-COLCHICINE; ENTRY Multiple languages Chemistry, Organic Multiple languages
URI:	http://kups.ub.uni-koeln.de/id/eprint/56621