Research output: Contribution to Journal/Magazine › Journal article › peer-review
Research output: Contribution to Journal/Magazine › Journal article › peer-review
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TY - JOUR
T1 - Organolithium-mediated conversion of beta-alkoxy aziridines into allylic sulfonamides
T2 - effect of the N-sulfonyl group and a formal synthesis of (+/-)-perhydrohistrionicotoxin
AU - Coote, Susannah C.
AU - Moore, Stephen P.
AU - O'Brien, Peter
AU - Whitwood, Adrian C.
AU - Gilday, John
PY - 2008/10/3
Y1 - 2008/10/3
N2 - 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.
AB - 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.
KW - TERMINAL AZIRIDINES
KW - LITHIATION
KW - AMINES
KW - ALCOHOLS
KW - OXIRANYL
KW - REAGENTS
KW - OLEFINS
KW - UTILITY
KW - ANIONS
KW - ROUTE
U2 - 10.1021/jo801586h
DO - 10.1021/jo801586h
M3 - Journal article
VL - 73
SP - 7852
EP - 7855
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 19
ER -