Organolithium-Mediated Conversion of β-Alkoxy Aziridines into Allylic Sulfonamides: Effect of the N-Sulfonyl Group and a Formal Synthesis of (±)-Perhydrohistrionicotoxin†

Susannah Coote, Steven Moore, Peter O'Brien, Adrian C. Whitwood, John Gilday

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17 Citations (SciVal)

Abstract

In 18 out of 20 examples of the organolithium-mediated conversion of β-alkoxy aziridines into substituted allylic sulfonamides, use of a Bus (Bus = t-BuSO2) substituent on the nitrogen gave higher yields compared to the analogous N-Ts compounds. The success with the N-Bus aziridines facilitated the development of a new route to the spirocyclic core of the histrionicotoxins and completion of a formal synthesis of (±)-perhydrohistrionicotoxin.
Original languageEnglish
Pages (from-to)7852-7855
Number of pages4
JournalJournal of Organic Chemistry
Volume73
Issue number19
DOIs
Publication statusPublished - 20 Sept 2008

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