Universität zu Köln

Shchegravina, Ekaterina S., Svirshchevskaya, Elena V., Schmalz, Hans-Guenther ORCID: 0000-0003-0489-1827 and Fedorov, Alexey Yu (2019). A Facile Synthetic Approach to Nonracemic Substituted Pyrrolo-allocolchicinoids Starting from Natural Colchicine. Synthesis, 51 (7). S. 1611 - 1623. STUTTGART: GEORG THIEME VERLAG KG. ISSN 1437-210X

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Abstract

A six-step semisynthetic approach towards chiral nonracemic pyrrolo-allocolchicinoids starting from naturally occurring colchicine was developed. The synthetic scheme includes an electrocyclic tropolone ring contraction to afford allocolchicinic acid followed by the Curtius reaction, giving the corresponding aniline. The Sandmeyer reaction and copper-mediated hydrazination gave hydrazine-substituted allocolchicine. This was introduced into the Fischer indole synthesis, affording libraries of regioisomeric indole-based allocolchicine congeners.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Shchegravina, Ekaterina S. UNSPECIFIED UNSPECIFIED UNSPECIFIED Svirshchevskaya, Elena V. UNSPECIFIED UNSPECIFIED UNSPECIFIED Schmalz, Hans-Guenther UNSPECIFIED orcid.org/0000-0003-0489-1827 UNSPECIFIED Fedorov, Alexey Yu UNSPECIFIED UNSPECIFIED UNSPECIFIED
URN:	urn:nbn:de:hbz:38-152394
DOI:	10.1055/s-0037-1610673
Journal or Publication Title:	Synthesis
Volume:	51
Number:	7
Page Range:	S. 1611 - 1623
Date:	2019
Publisher:	GEORG THIEME VERLAG KG
Place of Publication:	STUTTGART
ISSN:	1437-210X
Language:	English
Faculty:	Faculty of Mathematics and Natural Sciences
Divisions:	Faculty of Mathematics and Natural Sciences > Department of Chemistry > Institute of Organic Chemistry
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language BIOLOGICAL EVALUATION; ANTICANCER AGENTS; TUBULIN; ANALOGS; INHIBITORS; BINDING; PRODUCTS; INDOLES; METHYL Multiple languages Chemistry, Organic Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/15239