Sterically Accessible Catalysts for Hindered Substrates

By: William Sommer , Aldrich ChemFiles 2009,9.6, 5.

Aldrich ChemFiles 2009,9.6, 5.

More recently, Stoltz and Grubbs jointly reported the use of ringclosing metathesis in the key step of the total synthesis of (+)–elatol, a spiro[5.5]undecane-containing natural product which has drawn significant interest due to its antibiofueling, antibacterial, and antifungal activity as well as its cytotoxicity. The researchers developed an asymmetric synthesis of this molecule utilizing RCM (with Hoveyda- Grubbs 2nd Generation catalyst) in order to provide a key intermediate en route to the natural product. (Scheme 5).1

Scheme 5

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  1. White, D. E. et al. J. Am.Chem. Soc. 2008, 130, 810.

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