Synthesis of macrocyclic natural products by catalyst-controlled stereoselective ring-closing metathesis

Miao Yu, Chenbo Wang, Andrew F. Kyle, Pavol Jakubec, Darren J. Dixon, Richard R. Schrock and Amir H. Hoveyda ()
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Miao Yu: Merkert Chemistry Center, Boston College
Chenbo Wang: Merkert Chemistry Center, Boston College
Andrew F. Kyle: Chemistry Research Laboratory, University of Oxford
Pavol Jakubec: Chemistry Research Laboratory, University of Oxford
Darren J. Dixon: Chemistry Research Laboratory, University of Oxford
Richard R. Schrock: Massachusetts Institute of Technology
Amir H. Hoveyda: Merkert Chemistry Center, Boston College

Nature, 2011, vol. 479, issue 7371, 88-93

Abstract: Stereoselective ring closure There are a large number of chemical transformations in which alkenes act as the reactants and/or products of the reaction. Perhaps the most widely utilized approach to synthesis of unsaturated large rings is catalytic ring-closing metathesis (RCM), but this reaction often proceeds with little control over alkene. Amir Hoveyda and colleagues have developed a method for highly efficient and stereoselective synthesis of macrocyclic alkenes by catalytic RCM. It involves catalytic Z-isomer-selective cross-metathesis reactions of terminal enol ethers, which have not been reported previously, and allylic amides, used previously only in E-isomer-selective processes. The effectiveness of the method is demonstrated by the stereoselective synthesis of anticancer agents epothilone C and nakadomarin A.

Date: 2011
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DOI: 10.1038/nature10563

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