Synthesis of Tetrasubstituted Olefins

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

Aldrich ChemFiles 2009,9.6, 5.

In their preparation of sominone (R = OH, 22ß-O) and related analogs, Matsuya and coworkers used RCM to generate tetrasubstituted olefins. The RCM reaction was utilized in the preparation of the lactone side chain (Scheme 6). While ring closure affording the tetrasubstituted olefin with the Hoveyda-Grubbs catalyst (2nd Generation) proceeded in low yields (15–24%), it allowed a rapid and modular entry into the desired motif.1

Scheme 6

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Materials

     

References

  1. Matsuya, Y. et al. Org. Lett. 2009, 11, 3970.

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