| SZCZEPANIK, Pawel Marcin, Andrey MIKHAYLOV, Ondřej HYLSE, Roman KUČERA, Petra DAĎOVÁ, Marek NEČAS, Lukáš KUBALA, Kamil PARUCH and Jakub ŠVENDA. Convergent Assembly of the Tricyclic Labdane Core Enables Synthesis of Diverse Forskolin-like Molecules. Angewandte Chemie International Edition. Wiley, 2023, vol. 62, No 1, p. 1-7. ISSN 1433-7851. Available from: 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 and Jakub ŠVENDA. Convergent Assembly of the Tricyclic Labdane Core Enables Synthesis of Diverse Forskolin-like Molecules. \textit{Angewandte Chemie International Edition}. Wiley, 2023, vol.~62, No~1, p.~1-7. ISSN~1433-7851. Available from: https://dx.doi.org/10.1002/anie.202213183.
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