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Allylative Approaches to the Synthesis of Complex Guaianolide Sesquiterpenes from and .

著者 Hu X , Musacchio AJ , Shen X , Tao Y , Maimone TJ
J Am Chem Soc.2019 Aug 25 ; ():.
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With hundreds of unique members isolated to date, guaianolide lactones represent a particularly prolific class of terpene natural products. Given their extensive documented therapeutic properties and fascinating chemical structures, these metabolites have captivated the synthetic chemistry community for many decades. As a result of divergent biosynthetic pathways, which produce a wide array of stereochemical and oxidative permutations, a unifying synthetic pathway to this broad family of natural products is challenging. Herein we document the evolution of a chiral pool-based synthetic program aimed at accessing an assortment of guaianolides, particularly those from the plant family as well as , members of which possess distinct chemical substructures and necessitate deviating synthetic platforms. An initial route employing the linear monoterpene linalool generated a lower oxidation state guaianolide, but was not compatible with the majority of family members. A double allylation disconnection using a carvone-derived fragment was then developed to access first an -type guaianolide and then various congeners. Finally, using these findings in conjunction with a tandem polyoxygenation cascade, we developed a pathway to highly-oxygenated nortrilobolide. A variety of interesting observations in metal-mediated aldehyde allylation and alkene polyoxygenation are reported and discussed.
PMID: 31448610 [PubMed - as supplied by publisher]
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