Müller Nicolas, Kováč Ondřej, Rode Alexander, Atzl Daniel, Magauer Thomas
Department of Organic Chemistry and Center for Molecular Biosciences, University of Innsbruck Innrain 80-82 6020 Innsbruck, Austria.
Department of Organic Chemistry Palacký University Olomouc Tr. 17. Listopadu 12 77900 Olomouc, Czech Republic.
Synlett. 2025 Jan 24. doi: 10.1055/a-2501-4079.
We present our synthetic endeavors towards the meroterpenoid ganoapplanin. This natural product was isolated from a 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. 1Introduction2Synthesis of the Southern Terpenoid Fragment3Synthesis of the Northern Terpenoid Fragment4Triethylborane Mediated Giese Cyclization/Aldol Reaction Cascades5Completion of the Total Synthesis of Ganoapplanin6Conclusion.
我们展示了我们针对半萜类化合物ganoapplanin的合成研究。这种天然产物于2016年从一种真菌中分离出来，被发现是T型电压门控钙通道的抑制剂。我们的合成方法基于一种强大的分子内吉斯环化/分子间羟醛缩合级联反应，将北部的芳香片段与南部的萜类片段连接起来。本文重点介绍了合成研究，这些研究最终成功开发了关键的级联反应，最终实现了ganoapplanin的首次全合成。1引言2南部萜类片段的合成3北部萜类片段的合成4三乙基硼介导的吉斯环化/羟醛反应级联5ganoapplanin全合成的完成6结论
