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

Autor: Jacob G. Robins, Jeffrey S. Johnson
Jazyk: angličtina
Rok vydání: 2021
Předmět:
Zdroj: Org Lett
Popis: 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.
Databáze: OpenAIRE