Total synthesis and isolation of citrinalin and cyclopiamine congeners

Eduardo V. Mercado-Marin, Pablo Garcia-Reynaga, Stelamar Romminger, Eli. F. Pimenta, David K. Romney, Michael W. Lodewyk, David E. Williams, Raymond J. Andersen, Scott J. Miller, Dean J. Tantillo, Roberto G. S. Berlinck () and Richmond Sarpong ()
Additional contact information
Eduardo V. Mercado-Marin: University of California
Pablo Garcia-Reynaga: University of California
Stelamar Romminger: Instituto de Quimica de Sao Carlos, Universidade de Sao Paulo, CP 780, CEP 13560-970, Sao Carlos, SP, Brazil
Eli. F. Pimenta: Instituto de Quimica de Sao Carlos, Universidade de Sao Paulo, CP 780, CEP 13560-970, Sao Carlos, SP, Brazil
David K. Romney: Yale University, PO Box 208107, New Haven, Connecticut 06520, USA
Michael W. Lodewyk: University of California
David E. Williams: University of British Columbia, Vancouver, British Columbia V6T IZI, Canada
Raymond J. Andersen: University of British Columbia, Vancouver, British Columbia V6T IZI, Canada
Scott J. Miller: Yale University, PO Box 208107, New Haven, Connecticut 06520, USA
Dean J. Tantillo: University of California
Roberto G. S. Berlinck: Instituto de Quimica de Sao Carlos, Universidade de Sao Paulo, CP 780, CEP 13560-970, Sao Carlos, SP, Brazil
Richmond Sarpong: University of California

Nature, 2014, vol. 509, issue 7500, 318-324

Abstract: Abstract Many natural products that contain basic nitrogen atoms—for example alkaloids like morphine and quinine—have the potential to treat a broad range of human diseases. However, the presence of a nitrogen atom in a target molecule can complicate its chemical synthesis because of the basicity of nitrogen atoms and their susceptibility to oxidation. Obtaining such compounds by chemical synthesis can be further complicated by the presence of multiple nitrogen atoms, but it can be done by the selective introduction and removal of functional groups that mitigate basicity. Here we use such a strategy to complete the chemical syntheses of citrinalin B and cyclopiamine B. The chemical connections that have been realized as a result of these syntheses, in addition to the isolation of both 17-hydroxycitrinalin B and citrinalin C (which contains a bicyclo[2.2.2]diazaoctane structural unit) through carbon-13 feeding studies, support the existence of a common bicyclo[2.2.2]diazaoctane-containing biogenetic precursor to these compounds, as has been proposed previously.

Date: 2014
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DOI: 10.1038/nature13273

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