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

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

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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.

Item Type:
Journal Article
Journal or Publication Title:
Journal of Organic Chemistry
Uncontrolled Keywords:
/dk/atira/pure/subjectarea/asjc/1600/1605
Subjects:
ID Code:
72306
Deposited By:
Deposited On:
05 Jan 2015 11:26
Refereed?:
Yes
Published?:
Published
Last Modified:
19 Feb 2020 08:19