(–)‐Isosteviol as a Versatile Ex‐Chiral‐Pool Building Block for Organic Chemistry

Abstract

(–)‐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.

Application of Rigidity‐Controlled Supramolecular Affinity Materials for the Gravimetric Detection of Hazardous and Illicit Compounds

“…Stevioside is better known as a naturally occurring sweetener . (−)‐Isosteviol 3 exhibits functional groups arranged in a concave fashion and a well‐defined geometry to construct large and rigid molecular architectures . In our recent study, the combination of (−)‐isosteviol derivatives with another rigid building block allowed the construction of efficient affinity materials …”

“…[15] (À)-Isosteviol 3 exhibits functionalg roups arranged in ac oncave fashion and aw ell-definedg eometry to construct large and rigid molecular architectures. [16][17][18][19][20] In our recents tudy,t he combination of (À)isosteviol derivatives with another rigidb uilding block allowed the construction of efficient affinity materials. [21] Ac ombination of the core structures 1 or 2 with the (À)-isosteviol-derived building block enables affinity materials with defined cavities and more than one binding moiety for the guest molecules.…”

Design, synthesis and cytotoxic evaluation of nitric oxide‐releasing derivatives of isosteviol

“…Isosteviol is a tetracyclic diterpenoid with a beyerane skeleton, obtained by acid hydrolysis of crude glycoside fraction extracted from Stevia rebaudiana Bertoni . Recently, isosteviol has attracted growing interest of scientists because of its unique structure, easy accessibility and considerable pharmacological activities, especially in structural modification. By far, chemical modifications have been focused on CH 2 group at C‐15 position, the carbonyl at C‐16 position and the COOH group at C‐19 position.…”

Open-Chain and Macrocyclic Polyethyleneglycol Esters of the Diterpenoid Isosteviol

“…Greater than 150 isosteviol derivatives have been reported [2]. We previously synthesized open-chain dinuclear isosteviol derivatives in which two ent-beyerane moieties were connected by polymethylene spacers with terminal esters via the reactions of isosteviol chloride with diols and of 16-dihydroisosteviol (8) with dibasic carboxylic acid chlorides [3,4].…”