Cromolyn sodium, developed in the 1960s, has been used to prevent allergic reactions primarily affecting the lungs, as, for example, exercise-induced emphysema. It is thought to block the release of histamine, which prevents the sequence of events leading to swelling, itching, and constriction of bronchial tubes. Cromolyn sodium is synthesized in the following series of steps. Treatment of one mole of epichlorohydrin with two moles of 2,6-dihydroxyacetophenone in the presence of base gives I. Treatment of I with two moles of diethyl oxalate in the presence of sodium ethoxide gives a diester II. Saponification of the diester with aqueous NaOH gives cromolyn sodium.
Q. Is cromolyn sodium chiral? If so, which of the possible stereoisomers are formed
in this synthesis?
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