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