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Convergent Assembly of the Tricyclic Labdane Core Enables Synthesis of Diverse Forskolin-like Molecules
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SYSNO ASEP 0569310 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Convergent Assembly of the Tricyclic Labdane Core Enables Synthesis of Diverse Forskolin-like Molecules Author(s) Szczepanik, P. M. (CZ)
Mikhaylov, A. A. (CZ)
Hylse, O. (CZ)
Kučera, R. (CZ)
Daďová, Petra (BFU-R) ORCID
Nečas, M. (CZ)
Kubala, Lukáš (BFU-R) RID, ORCID
Paruch, K. (CZ)
Svenda, J. (CZ)Number of authors 9 Article number e202213183 Source Title Angewandte Chemie - International Edition. - : Wiley - ISSN 1433-7851
Roč. 62, č. 1 (2023)Number of pages 7 s. Publication form Online - E Language eng - English Country DE - Germany Keywords Convergent Synthesis ; Forskolin ; Labdanes ; Michael Addition ; Olefin Metathesis Subject RIV CE - Biochemistry OECD category Organic chemistry Method of publishing Open access Institutional support BFU-R - RVO:68081707 UT WOS 000892031600001 EID SCOPUS 85143281358 DOI 10.1002/anie.202213183 Annotation 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. Workplace Institute of Biophysics Contact Jana Poláková, polakova@ibp.cz, Tel.: 541 517 244 Year of Publishing 2024 Electronic address https://onlinelibrary.wiley.com/doi/10.1002/anie.202213183
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