Rearrangements to Electron-Deficient Carbon

1. Natural Products: Interconversions of terpenes. Click on a reaction to see the mechanism.
   1. Conversion of nerol and geraniol into a-terpineol and terpin.

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2. Conversion of myrcene into boll weevil sex pheromones.
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3. Conversion of nerolidol into bisabolene and bisabolol.

   

    

    

4. Conversion of squalene into lanosterol.

   

    

   

   Exercises: (a) Lanosterol is a triterpene consisting of two sesquiterpene units connected tail to tail. Find the isoprene units in lanosterol (see Chapter 18 in Ege for a review of the terpenes). (b) Cholesterol is produced from lanosterol by enzymes in the liver. What connectivity changes does lanosterol undergo in this transformation? Circle the parts of lanosterol that are changed in the transformation.