in addition to four vicinal diols that have their own stereochemistry. Brosa installed the hydroxyl groups in the steroid using both Woodward conditions to yield a cis-diol to the A ring of the steroid. Then, the alkene chain on the D ring was dihydroxylated to yield the second cis-diol using OsO4 and NMO as the stoichiometric oxidant. References Chemical processes Alkenes Diols