The synthesis and reactivity of β,γ-acetylenic and allenic sulfoxides and sulfones of dehydroepiandrosterone and their reactions with 1-butanethiol and glucose-6-phosphate dehydrogenase

The synthesis of the β,γ-acetylenic sulfoxide 2a and sulfone 2b of 3β-hydroxy-androst-5-en-17-one (dehydroepiandrosterone, DHEA) 1a are described. Isomerization of the β,γ-acetylenes 2a,b to their respective allenes 3a,b and their reactions with the nucleophile 1-butane-thiol, and glucose-6-phosphate dehydrogenase were studied.