Georg Thieme Verlag KG
Synthesis
,  volume 51 ,  issue 07 ,  pages 1611-1622

A Facile Synthetic Approach to Nonracemic Substituted Pyrrolo-allocolchicinoids Starting from Natural Colchicine

Publication type: Journal Article
Publication date: 2018-12-13
Georg Thieme Verlag KG
scimago Q2
wos Q2
SJR: 0.559
CiteScore: 4.6
Impact factor: 2.3
ISSN: 00397881, 1437210X
Catalysis
Organic Chemistry
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.

Found 
Found 
3 citations
Fedorov Alexey
DSc in Chemistry, associate member of the Russian Academy of Sciences 
93 publications,  2 825 citations,  10 reviews
h-index: 27
Lobachevsky State University of Nizhny Novgorod
Lobachevsky State University of Nizhny Novgorod
2 citations
Aksenov Aleksandr
🥼 🤝
DSc in Chemistry, professor
243 publications,  2 187 citations,  15 reviews
h-index: 24
North Caucasus Federal University
North Caucasus Federal University
Research interests
Medicinal Chemistry
Organic Chemistry
2 citations
Sosnovskikh Vyacheslav
DSc in Chemistry, professor
355 publications,  4 721 citations
h-index: 30
Ural Federal University
Ural Federal University
1 citation
Beloglazkina Elena
DSc in Chemistry, professor
296 publications,  3 248 citations,  11 reviews
h-index: 29
Lomonosov Moscow State University
Lomonosov Moscow State University
1 citation
Yaremenko Ivan
PhD in Chemistry
60 publications,  1 567 citations,  5 reviews
h-index: 24
N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences
N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences
Research interests
Organic Chemistry
1 citation
Gorbunova Yuliya
DSc in Chemistry, professor, full member of the Russian Academy of Sciences 
284 publications,  4 398 citations,  65 reviews
h-index: 34
Lomonosov Moscow State University
Lomonosov Moscow State University
Kurnakov Institute of General and Inorganic Chemistry of the Russian Academy of Sciences
Kurnakov Institute of General and Inorganic Chemistry of the Russian Academy of Sciences
A.N. Frumkin Institute of Physical Chemistry and Electrochemistry of the Russian Academy of Sciences
A.N. Frumkin Institute of Physical Chemistry and Electrochemistry of the Russian Academy of Sciences
Research interests
Coordination Chemistry
Lanthanides
Supramolecular chemistry
Tetrapyrrolic compounds
1 citation
Volcho Konstantin
DSc in Chemistry, professor of the Russian Academy of Sciences 
279 publications,  3 898 citations,  65 reviews
h-index: 31
N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry of the Siberian Branch of the Russian Academy of Sciences
N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry of the Siberian Branch of the Russian Academy of Sciences
1 citation
Danilkina Natalia
44 publications,  625 citations
h-index: 14
Saint Petersburg State University
Saint Petersburg State University
Research interests
Bioorganic chemistry
Click chemistry
Heterocyclic compounds
Medicinal Chemistry
Organic Chemistry
1 citation
Osipov Sergey
DSc in Chemistry
138 publications,  2 739 citations,  3 reviews
h-index: 29
A.N.Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences
A.N.Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences
1 citation
Gazizov Almir
🥼
DSc in Chemistry
157 publications,  889 citations,  23 reviews
h-index: 14
A.E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center of the Russian Academy of Sciences
A.E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center of the Russian Academy of Sciences
Research interests
Heterocyclic compounds
Organic Chemistry
Organophosphorus chemistry
1 citation
Karasik Andrey
DSc in Chemistry, professor, associate member of the Russian Academy of Sciences 
224 publications,  2 599 citations
h-index: 26
A.E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center of the Russian Academy of Sciences
A.E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center of the Russian Academy of Sciences
Research interests
Coordination Chemistry
Luminescence
Phosphorus ligands
1 citation
Dotsenko Viktor
DSc in Chemistry, professor
244 publications,  2 741 citations,  2 reviews
h-index: 22
North Caucasus Federal University
North Caucasus Federal University
Kuban State University
Kuban State University
Research interests
Active methylene compounds
Biological activity
Heterocyclic compounds
Malononitrile
Selenoamides
Thioamides
1 citation
Zagidullin Almaz
🥼 🤝
PhD in Chemistry
81 publications,  884 citations
h-index: 17
A.E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center of the Russian Academy of Sciences
A.E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center of the Russian Academy of Sciences
Research interests
Asymmetric metal complex catalysis
Chemistry of organic and organoelement compounds; chemistry of polymers; production of materials
Coordination chemistry of phosphorus
Organoelement chemistry
Organophosphorus chemistry
Synthesis of chiral phosphorus-containing ligands
1 citation
Ilkin Vladimir
PhD in Chemistry
16 publications,  187 citations
h-index: 7
Ural Federal University
Ural Federal University
Research interests
Catalysis
Heterocyclic compounds
Organic Chemistry
Synthetic Organic Chemistry
1 citation
Ivleva Elena
67 publications,  469 citations
h-index: 12
Samara State Technical University
Samara State Technical University
Research interests
Organic Chemistry
Organic synthesis
1 citation
Krylov Igor
PhD in Chemistry
78 publications,  1 885 citations,  18 reviews
h-index: 25
N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences
N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences
Research interests
Green chemistry
Organic Chemistry
Organic electrochemistry
Organic synthesis
Photochemistry
Plant protection
1 citation
Tikhomirov Alexander
🥼 🤝
DSc in Chemistry, associate professor
59 publications,  920 citations
h-index: 17
Mendeleev University of Chemical Technology of Russia
Mendeleev University of Chemical Technology of Russia
Gause Institute of New Antibiotics
Gause Institute of New Antibiotics
Research interests
Medicinal Chemistry
1 citation
Ivanov Andrey
54 publications,  534 citations
h-index: 12
A.E. Favorsky Irkutsk Institute of Chemistry of the Siberian Branch of the Russian Academy of Sciences
A.E. Favorsky Irkutsk Institute of Chemistry of the Siberian Branch of the Russian Academy of Sciences
1 citation
Buev Evgeny
PhD in Chemistry
31 publications,  346 citations,  2 reviews
h-index: 9
Ural Federal University
Ural Federal University
Research interests
Chemistry of nitrogen-containing heterocycles
Organic Chemistry
Organic synthesis

Top-30

Journals

1
Journal of Medicinal Chemistry
Journal of Medicinal Chemistry, 1, 11.11%
Journal of Medicinal Chemistry
1 publication, 11.11%
Tetrahedron
Tetrahedron, 1, 11.11%
Tetrahedron
1 publication, 11.11%
European Journal of Organic Chemistry
European Journal of Organic Chemistry, 1, 11.11%
European Journal of Organic Chemistry
1 publication, 11.11%
Russian Journal of General Chemistry
Russian Journal of General Chemistry, 1, 11.11%
Russian Journal of General Chemistry
1 publication, 11.11%
Journal of Enzyme Inhibition and Medicinal Chemistry
Journal of Enzyme Inhibition and Medicinal Chemistry, 1, 11.11%
Journal of Enzyme Inhibition and Medicinal Chemistry
1 publication, 11.11%
Organic and Biomolecular Chemistry
Organic and Biomolecular Chemistry, 1, 11.11%
Organic and Biomolecular Chemistry
1 publication, 11.11%
Russian Chemical Reviews
Russian Chemical Reviews, 1, 11.11%
Russian Chemical Reviews
1 publication, 11.11%
Russian Journal of Organic Chemistry
Russian Journal of Organic Chemistry, 1, 11.11%
Russian Journal of Organic Chemistry
1 publication, 11.11%
Журнал органической химии
Журнал органической химии, 1, 11.11%
Журнал органической химии
1 publication, 11.11%
1

Publishers

1
2
Pleiades Publishing
Pleiades Publishing, 2, 22.22%
Pleiades Publishing
2 publications, 22.22%
American Chemical Society (ACS)
American Chemical Society (ACS), 1, 11.11%
American Chemical Society (ACS)
1 publication, 11.11%
Elsevier
Elsevier, 1, 11.11%
Elsevier
1 publication, 11.11%
Wiley
Wiley, 1, 11.11%
Wiley
1 publication, 11.11%
Taylor & Francis
Taylor & Francis, 1, 11.11%
Taylor & Francis
1 publication, 11.11%
Royal Society of Chemistry (RSC)
Royal Society of Chemistry (RSC), 1, 11.11%
Royal Society of Chemistry (RSC)
1 publication, 11.11%
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii, 1, 11.11%
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
1 publication, 11.11%
The Russian Academy of Sciences
The Russian Academy of Sciences, 1, 11.11%
The Russian Academy of Sciences
1 publication, 11.11%
1
2
  • We do not take into account publications without a DOI.
  • Statistics recalculated weekly.

Are you a researcher?

Create a profile to get free access to personal recommendations for colleagues and new articles.
Metrics
9
Share
Cite this
GOST |
Cite this
GOST Copy
Schmalz H. et al. A Facile Synthetic Approach to Nonracemic Substituted Pyrrolo-allocolchicinoids Starting from Natural Colchicine // Synthesis. 2018. Vol. 51. No. 07. pp. 1611-1622.
GOST all authors (up to 50) Copy
Schmalz H., Shchegravina E., SVIRSHCHEVSKAYA E., Schmalz H. A Facile Synthetic Approach to Nonracemic Substituted Pyrrolo-allocolchicinoids Starting from Natural Colchicine // Synthesis. 2018. Vol. 51. No. 07. pp. 1611-1622.
RIS |
Cite this
RIS Copy
TY - JOUR
DO - 10.1055/s-0037-1610673
UR - https://doi.org/10.1055/s-0037-1610673
TI - A Facile Synthetic Approach to Nonracemic Substituted Pyrrolo-allocolchicinoids Starting from Natural Colchicine
T2 - Synthesis
AU - Schmalz, H.-G.
AU - Shchegravina, Ekaterina
AU - SVIRSHCHEVSKAYA, ELENA
AU - Schmalz, Hans-Günther
PY - 2018
DA - 2018/12/13
PB - Georg Thieme Verlag KG
SP - 1611-1622
IS - 07
VL - 51
SN - 0039-7881
SN - 1437-210X
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2018_Schmalz,
author = {H.-G. Schmalz and Ekaterina Shchegravina and ELENA SVIRSHCHEVSKAYA and Hans-Günther Schmalz},
title = {A Facile Synthetic Approach to Nonracemic Substituted Pyrrolo-allocolchicinoids Starting from Natural Colchicine},
journal = {Synthesis},
year = {2018},
volume = {51},
publisher = {Georg Thieme Verlag KG},
month = {dec},
url = {https://doi.org/10.1055/s-0037-1610673},
number = {07},
pages = {1611--1622},
doi = {10.1055/s-0037-1610673}
}
MLA
Cite this
MLA Copy
Schmalz, H.-G., et al. “A Facile Synthetic Approach to Nonracemic Substituted Pyrrolo-allocolchicinoids Starting from Natural Colchicine.” Synthesis, vol. 51, no. 07, Dec. 2018, pp. 1611-1622. https://doi.org/10.1055/s-0037-1610673.