A General Route to 3-Thiosubstituted Steroids via Copper-Catalyzed C–S Coupling

Abstract

A convenient and efficient approach to 3-thiosubstituted androstanes has been developed. The formation of a C(sp²)–S bond was achieved through the Cu-catalyzed coupling of steroidal iododienes with a variety of S-nucleophiles, such as (het)aryl thiols and dithiocarbamates. A simple catalytic system comprising CuI without auxiliary ligands enabled the preparation of a library of target compounds in good to high yields. A moderate inhibitory activity against hormone-dependent cancer cell lines was demonstrated for representative 3-thiolated steroids.

Key words

copper - catalysis - steroids - thiols - dithiocarbamates - heterocycles

Publikationsverlauf

Eingereicht: 18. November 2024

Angenommen nach Revision: 20. Januar 2025

Accepted Manuscript online:
20. Januar 2025

Artikel online veröffentlicht:
26. Februar 2025

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