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Issue 14, 2012
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Silver-promoted Friedel–Crafts reaction: concise total synthesis of (−)-ardeemin, (−)-acetylardeemin and (−)-formylardeemin

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Abstract

Total syntheses of multidrug resistant inhibitors (−)-acetylardeemin 2a, (−)-ardeemin 2b, and (−)-formylardeemin 3 have been achieved within 10 steps starting from bromopyrroloinoline 13. The key step involves direct alkylation of 13 with prenyl tributylstannane 11 to yield 12via a silver-promoted asymmetric Friedel–Crafts reaction. Highly efficient installation of the isoprenyl group allowed excellent overall yield. Moreover, the substrate scope of the asymmetric Friedel–Crafts reaction of 13 was expanded to include a variety of arenes 14 to afford natural product-like library analogues 15.

Graphical abstract: Silver-promoted Friedel–Crafts reaction: concise total synthesis of (−)-ardeemin, (−)-acetylardeemin and (−)-formylardeemin

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Publication details

The article was received on 03 Jan 2012, accepted on 30 Jan 2012 and first published on 02 Mar 2012


Article type: Paper
DOI: 10.1039/C2OB00014H
Citation: Org. Biomol. Chem., 2012,10, 2793-2797
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    Silver-promoted Friedel–Crafts reaction: concise total synthesis of (−)-ardeemin, (−)-acetylardeemin and (−)-formylardeemin

    Y. Wang, C. Kong, Y. Du, H. Song, D. Zhang and Y. Qin, Org. Biomol. Chem., 2012, 10, 2793
    DOI: 10.1039/C2OB00014H

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