Synthesis of Glabrescol

By: William Sommer, Aldrich ChemFiles 2009, 9.6, 7.

Aldrich ChemFiles 2009, 9.6, 7.

In 2000, Corey and coworkers utilized cross metathesis to synthesize a series of stereoisomers of glabrescol.1 Glabrescol is the biosynthetic precursor to steroids and triterpenoids. Upon preparation of the original structure proposed for glabrescol, it was realized the wrong structure for the natural product was reported. Corey and coworkers utilized a cross metathesis dimerization approach, which allowed for the preparation of the various isomers of glabrescol in a single step and ultimately lead to the correct structure assignment for glabrescol (Scheme 1).

Scheme 1

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Materials

     

References

  1. (a) Xiong, Z. et al. J. Am. Chem. Soc. 2000, 122, 4831. (b) Xiong, Z. et al. J. Am. Chem. Soc. 2000, 122, 9328.

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