Home > Research > Publications & Outputs > Organolithium-mediated conversion of beta-alkox...

Associated organisational unit

Links

Text available via DOI:

View graph of relations

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

Research output: Contribution to journalJournal article

Published
Close
<mark>Journal publication date</mark>3/10/2008
<mark>Journal</mark>Journal of Organic Chemistry
Issue number19
Volume73
Number of pages4
Pages (from-to)7852-7855
Publication statusPublished
Original languageEnglish

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.