Terpenoids are a very prominent class of natural compounds produced in diverse genera of plants, fungi, algae and sponges. They gained significant pharmaceutical value since prehistoric times, due to their broad spectrum of medical applications. The fragrant leaves of Eucalyptus trees are a rich source of terpenoids. Therefore this review starts by summarizing the main terpenoid compounds present in Eucalyptus globulus, E. citriodora, E. radiata and E. resinifera and describing their biosynthetic pathways. Of the enormous number of pharmaceutically important terpenoids, this paper also reviews some well established and recently discovered examples and discusses their medical applications. In this context, the synthetic processes for (–)-menthol, (–)-cis-carveol, (+)-artemisinine, (+)-merrilactone A and (–)-sclareol are presented. The tricyclic sesquiterpene (–)-englerin A isolated from the stem bark of the Phyllanthus engleri plant (Euphorbiaceae) is highly active against certain renal cancer cell lines. In addition, recent studies showed that englerin A is also a potent and selective activator of TRPC4 and TRPC5 calcium channels. These important findings were the motivation for several renowned research labs to achieve a total synthesis of (–)-englerin A. Two prominent examples – Christmann and Metz – are compared and discussed in detail.
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