Helvetica Chimica Acta p. 1168 - 1172 (1984)
Update date:2022-08-03
Topics:
Muchowski, Joseph M.
Naef, Reto
3-Lithio-1-(trimethylsilyl)pyrrole (7, Scheme 2), obtained by halogen-metal interchange from the 3-bromo compound 2, reacted with various electrophilic reagents to provide products, which on fluoride ion desilylation, gave 3-substituted pyrroles in good overall yields.One such pyrrole 13 (Scheme 3), was converted into 2-formyl-3-octadecylpyrrole (14), reputed to be a metabolite of the marine sponge Oscarella lobularis. 3,4-Dibromo-1-(triisopropylsilyl)pyrrole (5) was efficiently transformed, by a process involving two conscutive bromine-lithium exchange reactions (Scheme 4), into the antibiotic verrucarin E 17.
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(1984)
