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Synthesis 2019; 51(07): 1611-1622
DOI: 10.1055/s-0037-1610673
DOI: 10.1055/s-0037-1610673
paper
A Facile Synthetic Approach to Nonracemic Substituted Pyrrolo-allocolchicinoids Starting from Natural Colchicine
T This work was supported by the Russian Science Foundation (Project 16-13-10248).Further Information
Publication History
Received: 28 October 2018
Accepted after revision: 05 November 2018
Publication Date:
13 December 2018 (online)
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.
Key words
colchicine - pyrrolo-allocolchicinoids - Fischer indole synthesis - tubulin - anti-tubulin agentsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610673.
- Supporting Information
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