A Practical Synthesis of (2E,6E,8E)-N-(2-Methylpropyl)-2,6,8-hexadecatrien-10-ynamide

Ruthenium-Catalyzed Direct Dehydrogenative Cross-Coupling of Allyl Alcohols and Acrylates: Application to Total Synthesis of Hydroxy β-Sanshool, ZP-Amide I, and Chondrillin

“…It is surprising that, when we used allyl alcohol 2c as a coupling partner with methyl acrylate 1b , coupled product 3v was observed with double bond migration toward the ester side (instead of toward aldehyde) which was confirmed by NMR analysis with the reported data. , It is necessary to highlight that, to date, there is no report of synthesis of crucial intermediate 3v in a single step obtained under catalytic conditions. The traditional reported synthesis requires a five-step longest linear sequence to prepare 3v using a protection–deprotection strategy. , To further evaluate the efficiency and potential of this coupling reaction, a scale-up experiment was performed. Gram-scale synthesis of 3v by the reaction of allyl alcohol 2c (1.17g) with methyl acrylate (1.5 g) 1b gave identical results in terms of yield (1.47g, 60%) and stereoselectivity, indicating the robustness and practicality of this method.…”

“…The traditional reported synthesis requires a five-step longest linear sequence to prepare 3v using a protection−deprotection strategy. 44,45 To further evaluate the efficiency and potential of this coupling reaction, a scale-up experiment was performed. Gram-scale synthesis of 3v by the reaction of allyl alcohol 2c (1.17g) with methyl acrylate (1.5 g) 1b gave identical results in terms of yield (1.47g, 60%) and stereoselectivity, indicating the robustness and practicality of this method.…”