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Synfacts 2007(8): 0793-0793
DOI: 10.1055/s-2007-968715
DOI: 10.1055/s-2007-968715
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New YorkSynthesis of (±)-Marcfortine B
Contributor(s):Philip Kocienski, Fiona BlackB. M. Trost*, N. Cramer, H. Bernsmann
Stanford University, USA
Concise Total Synthesis of (±)-Marcfortine B
J. Am. Chem. Soc. 2007, 129: 3086-3087
Stanford University, USA
Concise Total Synthesis of (±)-Marcfortine B
J. Am. Chem. Soc. 2007, 129: 3086-3087
Further Information
Publication History
Publication Date:
24 July 2007 (online)
Key words
[3+2] cycloaddition - radical cyclization -
Significance
Marcfortine B is a secondary metabolite isolated from several Penicillium species. A trimethylenemethane [3+2] cycloaddition and a radical cyclization are used to construct two of the seven rings.
Comment
Treatment of xanthate ester D with AIBN and Bu3SnH generated alkene H rather than the expected piperidine compound. It is suggested that the secondary alkyl radical E reacts with AIBN and the resulting nitrogen-centered radical undergoes 1,4-hydrogen abstraction and subsequent elimination to afford H in 61% yield.