Total synthesis of diazonamide A

Robert R. Knowles, Joseph Carpenter, Simon B. Blakey, Akio Kayano, Ian K. Mangion, Christopher J. Sinz, David W.C. MacMillan

Research output: Contribution to journalArticle

101 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)308-311
Number of pages4
JournalChemical Science
Volume2
Issue number2
DOIs
StatePublished - 2011

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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    Knowles, R. R., Carpenter, J., Blakey, S. B., Kayano, A., Mangion, I. K., Sinz, C. J., & MacMillan, D. W. C. (2011). Total synthesis of diazonamide A. Chemical Science, 2(2), 308-311. https://doi.org/10.1039/c0sc00577k