Abstract
Ring closing metathesis (RCM) has emerged as a powerful tool to construct macrocyclic ring systems. However, the product distribution of monomer and oligomers is often a problem in the formation of medium to large rings. In the course of synthetic studies on the natural product radicicol and its analogs, we have found that the reaction temperature, along with concentration, has significant impact on the outcome of the product ratio. Specifically, carrying out the RCM reaction in refluxing toluene (110°C) at higher dilution affords improved yields of the monomeric macrocycle. Similar observations for another family of macrolactone natural products, the epothilones, are also reported.
| Original language | English |
|---|---|
| Pages (from-to) | 3297-3299 |
| Number of pages | 3 |
| Journal | Tetrahedron Letters |
| Volume | 44 |
| Issue number | 16 |
| DOIs | |
| Publication status | Published - 2003 Apr 14 |
| Externally published | Yes |
Keywords
- Epothilone
- Product distribution
- RCM
- Radicicol
- Ring closing metathesis
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry
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Cite this
Yamamoto, K., Biswas, K., Gaul, C., & Danishefsky, S. J. (2003). Effects of temperature and concentration in some ring closing metathesis reactions. Tetrahedron Letters, 44(16), 3297-3299. https://doi.org/10.1016/S0040-4039(03)00618-X