title: Organolithium-mediated conversion of beta-alkoxy aziridines into allylic sulfonamides: effect of the N-sulfonyl group and a formal synthesis of (+/-)-perhydrohistrionicotoxin.
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-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.
authors.affiliation: Department of Chemistry, University of York, Heslington, York YO10 5DD, UK.
authors.forename: Susannah C
authors.initials: SC
authors.lastname: Coote
authors.forename: Stephen P
authors.initials: SP
authors.lastname: Moore
authors.forename: Peter
authors.initials: P
authors.lastname: O'Brien
authors.forename: Adrian C
authors.initials: AC
authors.lastname: Whitwood
authors.forename: John
authors.initials: J
authors.lastname: Gilday
mesh_terms: D000664:Amphibian Venoms / Q000138:chemical synthesis*; D001388:Aziridines / Q000737:chemistry*; D008094:Lithium; D009942:Organometallic Compounds; D013449:Sulfonamides / Q000138:chemical synthesis*
chemical_list: D000664:Amphibian Venoms; D001388:Aziridines; D009942:Organometallic Compounds; D013449:Sulfonamides; C004792:perhydrohistrionicotoxin; D008094:Lithium