An Oxidative Dearomatization Approach to Tetrodotoxin via a Masked ortho-Benzoquinone.

Progress toward a stereoselective synthesis of tetrodotoxin (TTX) is presented. Oxidative dearomatization of a tetrasubstituted guaiacol arene yielded a masked ortho-benzoquinone that intercepted an acyl nitroso species generated in situ by the copper-catalyzed aerobic oxidation of an acyl hydroxylamine. The subsequent alkene dihydroxylation and reduction of a bis-neopentylic ketone proceeded with perfect diastereoselectivity to reveal advanced intermediates toward the synthesis of TTX.

Citation

Jacob G Robins, Jeffrey S Johnson. An Oxidative Dearomatization Approach to Tetrodotoxin via a Masked ortho-Benzoquinone. Organic letters. 2022 Jan 21;24(2):559-563

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PMID: 34968070

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