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Published January 9, 2013 | Published + Accepted Version + Supplemental Material
Journal Article Open

Stereoselective Access to Z and E Macrocycles by Ruthenium-Catalyzed Z-Selective Ring-Closing Metathesis and Ethenolysis


The first report of Z-selective macrocyclizations using a ruthenium-based metathesis catalyst is described. The selectivity for Z macrocycles is consistently high for a diverse set of substrates with a variety of functional groups and ring sizes. The same catalyst was also employed for the Z-selective ethenolysis of a mixture of E and Z macrocycles, providing the pure E isomer. Notably, an ethylene pressure of only 1 atm was required. These methodologies were successfully applied to the construction of several olfactory macrocycles as well as the formal total synthesis of the cytotoxic alkaloid motuporamine C.

Additional Information

© 2012 American Chemical Society. Received: November 15, 2012. Published: December 17, 2012. Dr. David VanderVelde is thanked for assistance with NMR experimentation and analysis. This work was financially supported by the NIH (R01-GM031332), the NSF (CHE-1212767), and the NSERC of Canada (fellowship to V.M.M.). Instrumentation on which this work was carried out was supported by the NIH (NMR spectrometer, RR027690). Materia, Inc. is thanked for its donation of metathesis catalyst 2.

Attached Files

Published - ja311241q.pdf

Accepted Version - nihms431317.pdf

Supplemental Material - ja311241q_si_001.pdf


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