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Issue 19, 2018
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Synthesis of the [7-5-5] tricyclic core of Daphniphyllum alkaloids

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Abstract

The [7-5-5] tricyclic core of the Daphniphyllum alkaloids was constructed, featuring a Claisen-Ireland rearrangement to install the two contiguous stereogenic centers, E1cB elimination to form the tetrasubstituted C–C double bond, and a 2,3-Wittig rearrangement to construct the quaternary carbon. Ring-closing metathesis and an intramolecular carbonyl ene reaction were employed for construction of the requisite ring system.

Graphical abstract: Synthesis of the [7-5-5] tricyclic core of Daphniphyllum alkaloids

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Publication details

The article was received on 12 Apr 2018, accepted on 18 Apr 2018 and first published on 18 Apr 2018


Article type: Communication
DOI: 10.1039/C8OB00859K
Citation: Org. Biomol. Chem., 2018,16, 3556-3559
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    Synthesis of the [7-5-5] tricyclic core of Daphniphyllum alkaloids

    Y. Kitabayashi, T. Fukuyama and S. Yokoshima, Org. Biomol. Chem., 2018, 16, 3556
    DOI: 10.1039/C8OB00859K

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