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Issue 2, 2011
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Total synthesis of diazonamide A

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A total synthesis of the marine natural product diazonamide A (1) has been accomplished. This work features a highly stereoselective synthesis of the C(10) quaternary center and the central furanoindoline core enabled by an iminium-catalyzed alkylation–cyclization cascade. Additionally, a magnesium-mediated intramolecular macroaldolization and a palladium-catalyzed tandem borylation/annulation were developed to enable the closure of the two 12-membered macrocycles of diazonamide A. This synthesis involves 20 steps in its longest linear sequence and proceeds in 1.8% overall yield.

Graphical abstract: Total synthesis of diazonamide A

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The article was received on 17 Nov 2010, accepted on 02 Dec 2010 and first published on 24 Dec 2010

Article type: Edge Article
DOI: 10.1039/C0SC00577K
Citation: Chem. Sci., 2011,2, 308-311
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    Total synthesis of diazonamide A

    R. R. Knowles, J. Carpenter, S. B. Blakey, A. Kayano, I. K. Mangion, C. J. Sinz and D. W. C. MacMillan, Chem. Sci., 2011, 2, 308
    DOI: 10.1039/C0SC00577K

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