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• W2041909595 abstract "The first total synthesis of (+)-8-epi-xanthatin (1) has been achieved in 14 steps starting from the commercially available ester 24, which was converted into aldehyde 23 in six steps. An enantioselective aldol reaction of 23 gave 30, which was transformed into triflate 22 in four steps, setting the stage for a palladium-catalyzed carbonylation reaction to form acrylate 34. Compound 34 was then subjected to a deprotection/lactonization sequence to furnish enyne 21, which underwent a domino enyne ring-closing metathesis/cross metathesis process to form a seven-membered carbocycle and (E)-conjugated dienone, thereby completing the synthesis of 1. This domino ruthenium-catalyzed metathesis reaction thus serves as an efficient method to construct the core of xanthanolide and other sesquiterpene lactones." @default.
• W2041909595 created "2016-06-24" @default.
• W2041909595 creator A5055989647 @default.
• W2041909595 creator A5071087545 @default.
• W2041909595 creator A5091424768 @default.
• W2041909595 date "2006-12-01" @default.
• W2041909595 modified "2023-10-18" @default.
• W2041909595 title "Domino intramolecular enyne metathesis/cross metathesis approach to the xanthanolides. Enantioselective synthesis of (+)-8-epi-xanthatin" @default.
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• W2041909595 doi "https://doi.org/10.1016/j.tet.2006.05.019" @default.
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