Convergent Assembly of the Tricyclic Labdane Core Enables Synthesis of Diverse Forskolin-like Molecules

Investor logo

Warning

This publication doesn't include Faculty of Sports Studies. It includes Faculty of Science. Official publication website can be found on muni.cz.
Authors

SZCZEPANIK Pawel Marcin MIKHAYLOV Andrey HYLSE Ondřej KUČERA Roman DAĎOVÁ Petra NEČAS Marek KUBALA Lukáš PARUCH Kamil ŠVENDA Jakub

Year of publication 2023
Type Article in Periodical
Magazine / Source Angewandte Chemie International Edition
MU Faculty or unit

Faculty of Science

Citation
Web https://doi.org/10.1002/anie.202213183
Doi http://dx.doi.org/10.1002/anie.202213183
Keywords Convergent Synthesis; Forskolin; Labdanes; Michael Addition; Olefin Metathesis
Description 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.
Related projects:

You are running an old browser version. We recommend updating your browser to its latest version.

More info