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CC BY-NC-ND 4.0 · Synlett
DOI: 10.1055/a-2501-4079
synpacts

Development of a Triethylborane Mediated Giese Cyclization/Aldol Reaction Cascade for the Total Synthesis of Ganoapplanin

Nicolas Müller 
1   Organic Chemistry, University of Innsbruck Faculty of Chemistry and Pharmacy, Innsbruck, Austria (Ringgold ID: RIN151267)
,
Ondřej Kováč
2   Chemistry, University of Innsbruck, Innsbruck, Austria (Ringgold ID: RIN27255)
,
Alexander Rode
2   Chemistry, University of Innsbruck, Innsbruck, Austria (Ringgold ID: RIN27255)
,
Daniel Atzl
2   Chemistry, University of Innsbruck, Innsbruck, Austria (Ringgold ID: RIN27255)
,
Thomas Magauer 
2   Chemistry, University of Innsbruck, Innsbruck, Austria (Ringgold ID: RIN27255)
› Author AffiliationsSupported by: Tiroler Wissenschaftsförderung F.33842/7-2021
Supported by: Austrian Science Fund 10.55776/P33894
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We present our synthetic endeavors towards the Ganoderma meroterpenoid ganoapplanin. This natural product was isolated from a Ganoderma fungus in 2016 and was found to be an inhibitor for T-type voltage-gated calcium channels. Our synthetic approach is based on a powerful intramolecular Giese cyclization/intermolecular aldol cascade to link the northern aromatic to the southern terpenoid fragment. This article highlights the synthetic studies that ultimately led to the successful development of the key cascade reaction, culminating in the first total synthesis of ganoapplanin.



Publication History

Received: 24 October 2024

Accepted after revision: 11 December 2024

Accepted Manuscript online:
12 December 2024

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