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Issue 14, 2019
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Asymmetric total synthesis of cryptoconcatone I

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Abstract

Asymmetric total synthesis of the naturally occurring cryptoconcatone I, which possesses a γ-Z-butenolide framework, is described here for the first time. Asymmetric propargylation, E-selective cross metathesis, and regioselective reductive epoxide ring opening were employed to access the enantiopure terminal alkyne. Late stage bimetallic cascade cyclization of the alkyne with (Z)-3-bromoacrylic acid afforded the natural product in an efficient way.

Graphical abstract: Asymmetric total synthesis of cryptoconcatone I

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Publication details

The article was received on 18 Feb 2019, accepted on 11 Mar 2019 and first published on 12 Mar 2019


Article type: Paper
DOI: 10.1039/C9OB00399A
Citation: Org. Biomol. Chem., 2019,17, 3552-3566

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    Asymmetric total synthesis of cryptoconcatone I

    R. K. Acharyya, P. Pal, S. Chatterjee and S. Nanda, Org. Biomol. Chem., 2019, 17, 3552
    DOI: 10.1039/C9OB00399A

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