The novel bis-addition of benzaldehydes to acrylates or maleates was achieved by the direct use of samarium metal with the assistance of CuI under mild conditions under dry air, and the useful 2-hydroxylalkyl-γ-butyrolactons and lignan derivatives were thus constructed with high efficiency. The key factors that influence the reaction efficiency were investigated. The use of potassium iodide and molecular sieves as additives can improve the reaction efficiency remarkably.

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In the presence of SmI3 and catalyzed by CuI in DMF, α-haloketones were transformed unexpectedly into α-hydroxy-1,4-diketones. The mechanism was probed and DMF was assumed to play a dual role both as a hydroxyl source and as a solvent.

Herein we report a unified strategy for the divergent total synthesis of six Elaeocarpus alkaloids in 6-10 steps from commercial available materials. This modular approach relied on the rapid construction...