A general and highly efficient diversity-oriented synthesis of tricyclic angularly fused-structured natural products, such as arteannuins, alliacanes, pentalenolactones and triquinanes, via selective cyclization from a common precursor is proposed.
The outlined synthetic methodology offers conceptually novel perspective, enabling to deliver multiple targets via cascade sequence of controlled intramolecular reactions from a common easily accessible key precursor; thus, providing simplified access to numerous classes of natural products, pharmaceutically important molecules and new potential therapeutic agents and drug candidates. Apparently, the mere existence of similar fundamental core structures is not exclusive to chemical compounds extracted from the same natural source. Common or highly resembling core structures were identified throughout various forms of life, such as different (and often distantly related) families of plants, as well as corals, fungi and bacteria. Examples include modern drugs and natural products derived from a broad spectrum of biological sources, such as Alliacol A, Artemisinine, Pentalenolactone P, Arteannuin M, and many others that share the tricyclic angularly fused ring systems. Even though previously developed synthetic methodologies towards the construction of the above mentioned molecules exist, the generality of our strategy and the ability to utilize simple and readily accessible precursors, will uncover rapid and efficient synthetic pathways to result in a wide range of natural products.
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