Diepoxide 11 and Triol 12 are involved in the synthesis of Ouabagenin, a steroid hormone which is difficult to produce by way of the step-by-step oxidation sequence typically achieved in nature using enzymes.  Because of this, a new approach utilizing both redox and oxidative stereochemical relays has been adapted as a basis for the scalable synthesis of polyhydroxylted steroids. The transformation from 11 to 12 specifically involves the reductive opening of the epoxide rings by way of an aluminum amalgam, using an on water technique.

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Citation: Renata, H.; Zhou, Q.; Baran, P. S. Science 2013, 339, 59-63.