| SZCZEPANIK, Pawel Marcin, Andrey MIKHAYLOV, Ondřej HYLSE, Roman KUČERA, Petra DAĎOVÁ, Marek NEČAS, Lukáš KUBALA, Kamil PARUCH a Jakub ŠVENDA. Convergent Assembly of the Tricyclic Labdane Core Enables Synthesis of Diverse Forskolin-like Molecules. Angewandte Chemie International Edition. Wiley, 2023, roč. 62, č. 1, s. 1-7. ISSN 1433-7851. Dostupné z: https://dx.doi.org/10.1002/anie.202213183. |
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@article{2249874,
author = {Szczepanik, Pawel Marcin and Mikhaylov, Andrey and Hylse, Ondřej and Kučera, Roman and Daďová, Petra and Nečas, Marek and Kubala, Lukáš and Paruch, Kamil and Švenda, Jakub},
article_number = {1},
doi = {http://dx.doi.org/10.1002/anie.202213183},
keywords = {Convergent Synthesis; Forskolin; Labdanes; Michael Addition; Olefin Metathesis},
language = {eng},
issn = {1433-7851},
journal = {Angewandte Chemie International Edition},
title = {Convergent Assembly of the Tricyclic Labdane Core Enables Synthesis of Diverse Forskolin-like Molecules},
url = {https://doi.org/10.1002/anie.202213183},
volume = {62},
year = {2023}
}
TY - JOUR
ID - 2249874
AU - Szczepanik, Pawel Marcin - Mikhaylov, Andrey - Hylse, Ondřej - Kučera, Roman - Daďová, Petra - Nečas, Marek - Kubala, Lukáš - Paruch, Kamil - Švenda, Jakub
PY - 2023
TI - Convergent Assembly of the Tricyclic Labdane Core Enables Synthesis of Diverse Forskolin-like Molecules
JF - Angewandte Chemie International Edition
VL - 62
IS - 1
SP - 1-7
EP - 1-7
PB - Wiley
SN - 14337851
KW - Convergent Synthesis
KW - Forskolin
KW - Labdanes
KW - Michael Addition
KW - Olefin Metathesis
UR - https://doi.org/10.1002/anie.202213183
N2 - 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.
ER -
SZCZEPANIK, Pawel Marcin, Andrey MIKHAYLOV, Ondřej HYLSE, Roman KUČERA, Petra DAĎOVÁ, Marek NEČAS, Lukáš KUBALA, Kamil PARUCH a Jakub ŠVENDA. Convergent Assembly of the Tricyclic Labdane Core Enables Synthesis of Diverse Forskolin-like Molecules. \textit{Angewandte Chemie International Edition}. Wiley, 2023, roč.~62, č.~1, s.~1-7. ISSN~1433-7851. Dostupné z: https://dx.doi.org/10.1002/anie.202213183.
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