Coote, Susannah C. and Moore, Stephen P. and O'Brien, Peter and Whitwood, Adrian C. and Gilday, John (2008) Organolithium-mediated conversion of beta-alkoxy aziridines into allylic sulfonamides : effect of the N-sulfonyl group and a formal synthesis of (+/-)-perhydrohistrionicotoxin. Journal of Organic Chemistry, 73 (19). pp. 7852-7855. ISSN 0022-3263
Full text not available from this repository.Abstract
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.