期刊
ORGANIC LETTERS
卷 24, 期 2, 页码 559-563出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c03998
关键词
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资金
- National Institute of General Medical Sciences [R35 GM118055]
- National Science Foundation [CHE-1726291]
- NSF MRI program [CHE-1828183, CHE-0922858]
Progress towards achieving a stereoselective synthesis of tetrodotoxin (TTX) is demonstrated in this research. By conducting oxidative dearomatization of a tetrasubstituted guaiacol arene and subsequent alkene dihydroxylation and reduction of a bis-neopentylic ketone, advanced intermediates towards the synthesis of TTX were successfully obtained with perfect diastereoselectivity.
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.
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