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Issue 5, 2012
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The intramolecular Diels–Alder reaction of tryptamine-derived Zincke aldehydes is a stepwise process

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Abstract

Computational studies show that the base-mediated intramolecular Diels–Alder of tryptamine-derived Zincke aldehydes, used as a key step in the synthesis of the Strychnos alkaloids norfluorocurarine and strychnine, proceeds via a stepwise pathway. The experimentally determined importance of a potassium counterion in the base is explained by its ability to preorganize the Zincke aldehyde diene in an s-cis conformation suitable to bicyclization. Computation also supports the thermodynamic importance of the generation of a stable enolate in the final reaction step. The thermal cycloreversion reaction of the Diels–Alder products is also found to proceed in a stepwise manner.

Graphical abstract: The intramolecular Diels–Alder reaction of tryptamine-derived Zincke aldehydes is a stepwise process

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Publication details

The article was received on 18 Dec 2011, accepted on 01 Feb 2012 and first published on 02 Feb 2012


Article type: Edge Article
DOI: 10.1039/C2SC01072K
Citation: Chem. Sci., 2012,3, 1650-1655
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    The intramolecular Diels–Alder reaction of tryptamine-derived Zincke aldehydes is a stepwise process

    H. V. Pham, D. B. C. Martin, C. D. Vanderwal and K. N. Houk, Chem. Sci., 2012, 3, 1650
    DOI: 10.1039/C2SC01072K

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