Abstract
Sesquiterpenoids constitute a marvelously varied group of natural products that feature a vast array of molecular architectures. Among them, the unusual bicyclo [6.3.0] undecane sesquiterpenoids are one of the most representative. To date, only approximately 42 naturally occurring compounds with this unique scaffold, which can be classified into seven different groups, have been reported. As the first-found member of each type, dactylol, asteriscanolide, dumortenol, toxicodenane C, and capillosanane S are characteristic of the four methyl groups on the five-eight-membered ring system. Only 11-hydroxyjasionone and sinuketal decorate the core with an isopropyl group. These natural products exhibit a wide range of bioactivities, including antifouling, anti-inflammatory, immune suppression, cytotoxic, antimutagenic, antiplasmodial, and antiviral activities. It was noted that some total syntheses of precapnellane-sesquiterpenoids (dactylol, poitediol, precapnelladiene), asteriscanolide, and 11-hydroxyjasionone have been achieved, because their cyclooctanoid core represents an important target for the development of synthetic strategies to prepare eight-membered ring-containing compounds. This review focuses on these natural sesquiterpenoids and their biological activities and synthesis, and aims to provide a foundation for further research of these interesting compounds.
Highlights
In the past thirty years, nature has played a significant role in the discovery of new drugs.many natural products with interesting skeletons have been reported from terrestrial and marine sources [1,2,3,4]
To provide a foundation for further research,biological this review summarizes foundationhas forbeen further research, this review summarizes the structures, activities, and the structures, biological activities, and chemical synthesis of bicyclo chemical synthesis of bicyclo [6.3.0] undecane sesquiterpenoids
Bicyclo [6.3.0] undecane sesquiterpenoids are relatively rare in nature
Summary
In the past thirty years, nature has played a significant role in the discovery of new drugs. The unusual bicyclo [6.3.0] undecane sesquiterpenoids are one of the most representative. Aplysia dactylomela in 1977 [9], only seven types of scaffolds of bicyclo [6.3.0] undecane dactylomela in 1977have [9], only types(Figure of scaffolds of bicyclo [6.3.0]. As the cyclooctanoid core represents an important and group. As thetarget cyclooctanoid represents of an important and challenging target the development challenging for the core development the methodology, necessary to for prepare the eightof the methodology, necessary to prepare the total eight-membered ring-containing compounds, some membered ring-containing compounds, some syntheses of precapnellane-sesquiterpenoid [10–. 29], asteriscane-sesquiterpenoid [30,31,32,33,34,35,36], and jasionane-sesquiterpenoid [37] have been achieved. Chemical synthesis of bicyclo [6.3.0] undecane sesquiterpenoids
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