Reduction of an a,-Unsaturated y-Diketone with Zinc

The reduction of ,/S-unsaturated y-diketones can conveniently be done with zinc in acetic acid. The following procedure is applicable to the reduction of the Diels-Alder adduct of quinone and butadiene (Chapter 8, Section II). 

Stork and S. D. Darling, J. Amer. Chem. Soc. 86, 1761 (1964) and references cited therein. 

The procedures given below are typical of the variety of applications of the hydroboration reaction. 

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