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DOI: 10.1055/a-2501-4079
Development of a Triethylborane-Mediated Giese Cyclization/Aldol Reaction Cascade for the Total Synthesis of Ganoapplanin
Authors
We acknowledge the Tiroler Wissenschaftsförderung (TWF, F.33842/ 7-2021 to N.M.) and the European Research Council under the European Union’s Horizon 2020 research and innovation program (grant agreement no. 101000060), the Österreichische Akademie der Wissenschaften (OeAW), and the Center for Molecular Biosciences (CMBI), University of Innsbruck. Dr. Ondřej Kováč is grateful to the Nadace Experientia for financial support.
Abstract
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.
1 Introduction
2 Synthesis of the Southern Terpenoid Fragment
3 Synthesis of the Northern Terpenoid Fragment
4 Triethylborane-Mediated Giese Cyclization/Aldol Reaction Cascades
5 Completion of the Total Synthesis of Ganoapplanin
6 Conclusion
Publication History
Received: 24 October 2024
Accepted after revision: 11 December 2024
Accepted Manuscript online:
12 December 2024
Article published online:
24 January 2025
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