An unexpected acid-catalyzed rearrangement of diacetoxy benzylidenespirostanes to spirochromene acetals and spiroindenes with radical scavenger activity

[Display omitted] •Diacetoxy Benzylidenespirostanes underwent unexpended rearrangement when treated with HCl/CH3OH in CH2Cl2.•Compounds bearing an acetoxy group at the ortho position produced spirochromenes.•Compounds with no substituent at the ortho position led to spiroindenes.•All the rearranged...

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Bibliographic Details
Published in:Steroids 2022-12, Vol.188, p.109110-109110, Article 109110
Main Authors: Ramos-Enríquez, Manuel A., Medina-Campos, Omar N., Pedraza-Chaverri, José, Flores-Álamo, Marcos, Iglesias-Arteaga, Martín A.
Format: Article
Language:English
Subjects:
Acetals
Acid catalyzed rearrangement
Antioxidants
Catalysis
Diacetoxybenzylidenespirostanes
Radical scavenger activity
Spirochromenes
Spiroindenes
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Summary:[Display omitted] •Diacetoxy Benzylidenespirostanes underwent unexpended rearrangement when treated with HCl/CH3OH in CH2Cl2.•Compounds bearing an acetoxy group at the ortho position produced spirochromenes.•Compounds with no substituent at the ortho position led to spiroindenes.•All the rearranged compounds exhibited moderate antioxidant activity. 23E-diacetoxybenzylidenespirostanes underwent rearrangement when treated with HCl in CH2Cl2/CH3OH. 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.
ISSN:0039-128X
1878-5867
DOI:10.1016/j.steroids.2022.109110