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Organolithium-mediated conversion of beta-alkoxy aziridines into allylic sulfonamides: effect of the N-sulfonyl group and a formal synthesis of (+/-)-perhydrohistrionicotoxin

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<mark>Journal publication date</mark>3/10/2008
<mark>Journal</mark>Journal of Organic Chemistry
Issue number19
Number of pages4
Pages (from-to)7852-7855
Publication StatusPublished
<mark>Original language</mark>English


In 18 out of 20 examples of the organolithium-mediated conversion of beta-alkoxy aziridines into substituted allylic sulfonamides, use of a Bus (Bus = t-BuSO(2)) 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.