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Issue 44, 2018
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Total synthesis of (±)-chondrosterin I using a desymmetric aldol reaction

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Abstract

The first total synthesis of racemic chondrosterin I was accomplished. The synthetic features include a Michael addition to incorporate a nitro alkane moiety, an oxidative Nef reaction, intramolecular cyclization of the γ-ketoester derivative, and a desymmetric intramolecular aldol reaction of the meso diketoester compound. The present strategy will be applicable to the synthesis of an optically active form by asymmetric desymmetrization.

Graphical abstract: Total synthesis of (±)-chondrosterin I using a desymmetric aldol reaction

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Publication details

The article was received on 15 Oct 2018, accepted on 18 Oct 2018 and first published on 24 Oct 2018


Article type: Communication
DOI: 10.1039/C8OB02557F
Citation: Org. Biomol. Chem., 2018,16, 8477-8480
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    Total synthesis of (±)-chondrosterin I using a desymmetric aldol reaction

    Y. Kawamoto, D. Ozone, T. Kobayashi and H. Ito, Org. Biomol. Chem., 2018, 16, 8477
    DOI: 10.1039/C8OB02557F

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