Reaction pathway for the synthesis of derivative 21

February 29, 2024

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  Reaction pathway for the synthesis of derivative 21

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• Tetraoxanes as inhibitors of apicomplexan parasites Plasmodium falciparum and Toxoplasma gondii growth and anti-cancer molecules

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  Scheme 1

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  The key intermediary tetraoxane amine 21 was prepared according to a previously described procedure (Scheme 1). In brief, cyclohexane was transformed into gem-dihydroperoxide 17 using 50% H₂O₂ in the presence of Re₂O₇ as catalyst, which was further coupled with benzyl 4-oxocyclohexanecarboxylate 15  producing tetraoxane benzyl ester 18. The presence of the benzyl-group enabled  a more efficacious purification of the crude product using a Biotage SP chromatography system. Reduction with LiAlH₄ produced alcohol 19, which was  transformed via the corresponding azide 20 into amine 21.