Jump to main content
Jump to site search

Issue 2, 2011
Previous Article Next Article

Total synthesis of diazonamide A

Author affiliations

Abstract

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

Back to tab navigation
Please wait while Download options loads

Supplementary files

Publication details

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
  •   Request permissions

    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

Search articles by author