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Issue 44, 2017
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Functional group manoeuvring for tuning stability and reactivity: synthesis of cicerfuran, moracins (D, E, M) and chromene-fused benzofuran-based natural products

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Abstract

The protecting group manoeuvring as a strategy was applied for tuning the stability and reactivity of 4-(2,2-dibromovinyl)benzene-1,3-diol (12a) and 6-(2,2-dibromovinyl)-2,2-dimethylchroman-7-ol (22) in the domino synthesis of benzofuran-based natural products (1–8). The functional group demands and their impact on the reactivity driven by electronic effects were successfully managed by varying the protecting groups with substituted gem-dibromovinylphenols in domino couplings and triarylbismuth reagents under palladium-catalyzed conditions. This approach paved the way for the synthesis of moracin M (1) and cicerfuran (2), and the first time synthesis of moracin D (3) and moracin E (4) along with chromene-fused benzofuran-based natural products (5–8) in overall good yields.

Graphical abstract: Functional group manoeuvring for tuning stability and reactivity: synthesis of cicerfuran, moracins (D, E, M) and chromene-fused benzofuran-based natural products

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Publication details

The article was received on 04 Oct 2017, accepted on 21 Oct 2017 and first published on 02 Nov 2017


Article type: Paper
DOI: 10.1039/C7OB02459B
Citation: Org. Biomol. Chem., 2017,15, 9415-9423
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    Functional group manoeuvring for tuning stability and reactivity: synthesis of cicerfuran, moracins (D, E, M) and chromene-fused benzofuran-based natural products

    M. L. N. Rao, V. N. Murty and S. Nand, Org. Biomol. Chem., 2017, 15, 9415
    DOI: 10.1039/C7OB02459B

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