Home / Articles / Synthesis of allocolchicinoids: a 50 year journey

Synthesis of allocolchicinoids: a 50 year journey

Nikolay Sergeyevich Sitnikov 1
Nikolay Sergeyevich Sitnikov
, 
1 N. I. Lobachevski State University of Nizhni Novgorod, Department of Chemistry
10.1070/RC2013v082n05ABEH004361
Published 30 November 2012
Communication , Volume 82, Issue 5, 393-411
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Sitnikov N. S., Fedorov A. Y. Synthesis of allocolchicinoids: a 50 year journey // Russian Chemical Reviews. 2013. Vol. 82. No. 5. pp. 393-411.
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Sitnikov N. S., Fedorov A. Y. Synthesis of allocolchicinoids: a 50 year journey // Russian Chemical Reviews. 2013. Vol. 82. No. 5. pp. 393-411.
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TY - JOUR
DO - 10.1070/RC2013v082n05ABEH004361
UR - https://rcr.colab.ws/publications/10.1070/RC2013v082n05ABEH004361
TI - Synthesis of allocolchicinoids: a 50 year journey
T2 - Russian Chemical Reviews
AU - Sitnikov, Nikolay Sergeyevich
AU - Fedorov, Alexey Yur'evich
PY - 2013
DA - 2012/11/30
PB - ANO Editorial Board of the journal Uspekhi Khimii
SP - 393-411
IS - 5
VL - 82
ER -
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@article{2013_Sitnikov,
author = {Nikolay Sergeyevich Sitnikov and Alexey Yur'evich Fedorov},
title = {Synthesis of allocolchicinoids: a 50 year journey},
journal = {Russian Chemical Reviews},
year = {2013},
volume = {82},
publisher = {ANO Editorial Board of the journal Uspekhi Khimii},
month = {Nov},
url = {https://rcr.colab.ws/publications/10.1070/RC2013v082n05ABEH004361},
number = {5},
pages = {393--411},
doi = {10.1070/RC2013v082n05ABEH004361}
}
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Sitnikov, Nikolay Sergeyevich, and Alexey Yur'evich Fedorov. “Synthesis of allocolchicinoids: a 50 year journey.” Russian Chemical Reviews, vol. 82, no. 5, Nov. 2013, pp. 393-411. https://rcr.colab.ws/publications/10.1070/RC2013v082n05ABEH004361.
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Abstract

Published data on the stereo- and enantioselective synthesis of allocolchicinoids, which are of interest as antitumour agents, are summarized. The stereochemical features of these compounds are described. Two key approaches to their preparation are considered, namely, the synthesis from natural colchicine and total synthesis from commercially available reagents. Various total syntheses of N-acetylcolchinol are performed using biaryl oxidative and reductive coupling, cyclopropanation–ring expansion and Nicholas reaction. The synthetic routes to allocolchicine are based on Diels–Alder cycloaddition, combination of Diels–Alder and metathesis reactions and direct catalytic CH-arylation. Analogues of the colchicine site ligands incorporating heteroaromatic rings are briefly considered; their structural features and methods of synthesis are discussed.

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