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Asymmetric total synthesis of (−)-δ-lycorane

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A first asymmetric synthesis of the lycorine-type Amaryllidaceae alkaloid (−)-δ-lycorane by using a chiral bifunctional squaramide-catalysed cascade reaction as a powerful tool to construct the skeleton of the alkaloid on the basis of unsaturated β-ketoester and nitroalkene is reported. The sequence afforded a highly functionalized intermediate with three stereogenic centres with high diastereoselectivity (>20 : 1 dr) and high enantioselectivity (92% ee) in one step, which was converted into (−)-δ-lycorane in eight steps.

Graphical abstract: Asymmetric total synthesis of (−)-δ-lycorane

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Publication details

The article was received on 08 Jan 2017, accepted on 01 Mar 2017 and first published on 02 Mar 2017

Article type: Research Article
DOI: 10.1039/C7QO00021A
Citation: Org. Chem. Front., 2017, Advance Article
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    Asymmetric total synthesis of (−)-δ-lycorane

    J. Wang, J. Li, X. Shen, C. Dong, J. Lin and K. Wei, Org. Chem. Front., 2017, Advance Article , DOI: 10.1039/C7QO00021A

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