23E-diacetoxybenzylidenespirostanes underwent rearrangement when treated with HCl in CHCl/CHOH. The course of the rearrangement depends on the substitution pattern in the phenyl ring. While compounds bearing an acetoxy group at the ortho position produced spirochromenes, the partners with no substituent at the ortho position led to spiroindenes. All the rearranged compounds exhibited moderate antioxidant activity.
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