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

2012/12/17 by Vanessa M. Marx, Myles B. Herbert, Benjamin K. Keitz +1 · 1 citation
Biochemistry, Genetics and Molecular Biology · Chemistry · Medicine · #Chemical Synthesis and Analysis #Microbial Natural Products and Biosynthesis #Synthetic Organic Chemistry Methods

paper · doi:10.1021/ja311241q

openalex publication_date 2012/12/17 · openalex created_date 2016/06/24 · openalex updated_date 2026/08/01

Abstract

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.

Citations

• Macrocyclization by Ring‐Closing Metathesis in the Total Synthesis of Natural Products: Reaction Conditions and Limitations

Cited by

• Ring-closing metathesis [wikipedia]

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