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.
Marx, Vanessa M.,Herbert, Myles B.,Keitz, Benjamin K.,Grubbs, Robert H.