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Synthesis 2024; 56(10): 1585-1592
DOI: 10.1055/s-0042-1751529
DOI: 10.1055/s-0042-1751529
paper
Bürgenstock Special Section 2022 – Future Stars in Organic Chemistry
Total Synthesis of Lucidumone: Attempted Shortcuts, Dead Ends and Lessons Learnt
This work was funded by the Université Paris-Saclay, Centre National de la Recherche Scientifique (CNRS), China Scholarship Council (PhD fellowship for G.H.) and LabEx CHARM3AT (postdoctoral fellowship for L.P.). The authors thank the funding organizations for support.
Abstract
Lucidumone is a meroterpenoid isolated from the mushroom Ganoderma lucidum, displaying selective COX-2 inhibitory activity. In this work, we detail our synthetic efforts which led to the first enantioselective synthesis of lucidumone in 13 steps (longest linear sequence). Beyond the key retro-[4+2]/intramolecular Diels–Alder cascade, we discuss the difficulties regarding fragment assembly, introduction of the methyl ketone moiety and choice of adequate protecting group.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0042-1751529.
- Supporting Information
Publication History
Received: 21 August 2023
Accepted after revision: 02 November 2023
Article published online:
04 December 2023
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