(–)‐Isosteviol is readily available in large quantities by the acidic treatment of a common alternative sweetener. The two functional groups of (–)‐isosteviol are presented on the same side of the ent‐beyerane scaffold with a mutual C–C distance of about 7 Å. Their unique concave arrangement experiences a strong asymmetric environment due to an adjacent methyl group. Consequently, this building block has found several applications in supramolecular chemistry and organocatalysis. These areas and the chemical modification of this scaffold as well as its biological activity are surveyed.
The cover picture shows the structure of (–)‐isosteviol, the functional groups of which create a kind of airfield for the interaction with other molecules, whereas the adjacent methyl tower causes an asymmetric environment. The rigid lipophilic backbone keeps this architecture, which exhibits similarities to an aircraft carrier floating on the interface. These structural features create a powerful and versatile ex‐chiral‐pool building block, which has recently found a wide application in various fields of organic chemistry. Waldvogel et al. provide a survey on (Aircraft Carrier: U.S. Navy photo by Mass Communication Specialist Seaman Iain L. Stratton, graphics C. Siering)
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