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Synthesis of the cytotrienin A core via metal catalyzed C-C coupling
Michael Rössle1, David J Del Valle, Michael J Krische
1University of Texas at Austin, Department of Chemistry and Biochemistry, Austin, Texas 78712, United States.
Abstract:
A synthetic approach to the C17-benzene ansamycins via metal catalyzed C-C coupling is described. Key bond formations include direct iridium catalyzed carbonyl crotylation from the alcohol oxidation level followed by chelation-controlled Sakurai-Seyferth dienylation to form the stereotriad, which is attached to the arene via Suzuki cross-coupling. The diene-containing carboxylic acid is prepared using rhodium catalyzed acetylene-aldehyde reductive C-C coupling mediated by gaseous hydrogen. Finally, ring-closing metathesis delivers the cytotrienin core.
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