Angewandte Chemie - International Edition, volume 62, issue 1
Convergent Assembly of the Tricyclic Labdane Core Enables Synthesis of Diverse Forskolin‐like Molecules
Paweł M Szczepanik
1, 2
,
Andrey A Mikhaylov
1, 2
,
Ondřej Hylse
1, 2
,
Roman Kučera
2
,
Petra Daďová
3, 4
,
Marek Nečas
2
,
Lukáš Kubala
1, 3, 4
,
Kamil Paruch
1, 2
,
Jakub Švenda
1, 2
1
International Clinical Research Center St. Anne's University Hospital Pekařská 53 Brno 656 91 Czech Republic
|
2
Department of Chemistry, Faculty of Science Masaryk University Kamenice 5 Brno 625 00 Czech Republic
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3
Institute of Biophysics Academy of Sciences of the Czech Republic Královopolská 135 Brno 612 65 Czech Republic
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4
Department of Experimental Biology Faculty of Science Masaryk University Kamenice 5 Brno 625 00 Czech Republic
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Publication type: Journal Article
Publication date: 2022-11-29
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 16.6
ISSN: 14337851, 15213773
General Chemistry
Catalysis
Abstract
We report a new synthetic strategy for the flexible preparation of forskolin-like molecules. The approach is different from the previously published works and employs a convergent assembly of the tricyclic labdane-type core from pre-functionalized cyclic building blocks. Stereoselective Michael addition enabled the fragment coupling with excellent control over three newly created contiguous stereocenters, all-carbon quaternary centers included. Silyl enol ether-promoted ring-opening metathesis paired with ring closure were the other key steps enabling concise assembly of the tricyclic core. Late-stage functionalization sequences transformed the tricyclic intermediates into a set of different forskolin-like molecules. The modular nature of the synthetic scheme described herein has the potential to become a general platform for the preparation of analogs of forskolin and other complex tricyclic labdanes.
Top-30
Citations by journals
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Chemistry and Biodiversity
1 publication, 25%
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Chemistry Africa
1 publication, 25%
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Russian Chemical Reviews
1 publication, 25%
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Chemistry - A European Journal
1 publication, 25%
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Citations by publishers
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2
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Wiley
2 publications, 50%
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Springer Nature
1 publication, 25%
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Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
1 publication, 25%
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- We do not take into account publications without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
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Szczepanik P. M. et al. Convergent Assembly of the Tricyclic Labdane Core Enables Synthesis of Diverse Forskolin‐like Molecules // Angewandte Chemie - International Edition. 2022. Vol. 62. No. 1.
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Szczepanik P. M., Mikhaylov A. A., Hylse O., Kučera R., Daďová P., Nečas M., Kubala L., Paruch K., Švenda J. Convergent Assembly of the Tricyclic Labdane Core Enables Synthesis of Diverse Forskolin‐like Molecules // Angewandte Chemie - International Edition. 2022. Vol. 62. No. 1.
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TY - JOUR
DO - 10.1002/anie.202213183
UR - https://doi.org/10.1002/anie.202213183
TI - Convergent Assembly of the Tricyclic Labdane Core Enables Synthesis of Diverse Forskolin‐like Molecules
T2 - Angewandte Chemie - International Edition
AU - Szczepanik, Paweł M
AU - Mikhaylov, Andrey A
AU - Hylse, Ondřej
AU - Kučera, Roman
AU - Daďová, Petra
AU - Nečas, Marek
AU - Kubala, Lukáš
AU - Paruch, Kamil
AU - Švenda, Jakub
PY - 2022
DA - 2022/11/29 00:00:00
PB - Wiley
IS - 1
VL - 62
SN - 1433-7851
SN - 1521-3773
ER -
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@article{2022_Szczepanik,
author = {Paweł M Szczepanik and Andrey A Mikhaylov and Ondřej Hylse and Roman Kučera and Petra Daďová and Marek Nečas and Lukáš Kubala and Kamil Paruch and Jakub Švenda},
title = {Convergent Assembly of the Tricyclic Labdane Core Enables Synthesis of Diverse Forskolin‐like Molecules},
journal = {Angewandte Chemie - International Edition},
year = {2022},
volume = {62},
publisher = {Wiley},
month = {nov},
url = {https://doi.org/10.1002/anie.202213183},
number = {1},
doi = {10.1002/anie.202213183}
}