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• W2023008615 startingPage "6611" @default.
• W2023008615 abstract "The diastereoselective PdCl2/CuCl2-catalysed intramolecular methoxyaminocarbonylation of N-benzyl protected alkenyl amine 4 was used as a key step in the total synthesis of the naturally occurring piperidine alkaloid (−)-pinidinone. Commercially available (S)-propylene oxide was employed as starting material, delivering the key substrate 4 in three steps and 68% overall yield. Subsequently, the influence of various reaction parameters on the diastereoselectivity of the key cyclisation of 4 was scrutinised. Copper(II) chloride proved to be the optimum reagent and/or co-catalyst for the successful aminocyclisation-methoxycarbonylation tandem transformation of alkenyl amine 4 into the desired methyl esters 3 and 8. The latter were subsequently transformed into the title natural product." @default.
• W2023008615 created "2016-06-24" @default.
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• W2023008615 date "2010-12-01" @default.
• W2023008615 modified "2023-10-16" @default.
• W2023008615 title "Synthesis of (−)-pinidinone" @default.
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• W2023008615 doi "https://doi.org/10.1016/j.tetlet.2010.10.049" @default.
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