J. Muchowski, R. Naef
Jun 20, 1984
Citations
0
Influential Citations
40
Citations
Journal
Helvetica Chimica Acta
Abstract
3-Lithio-1-(trimethylsilyl)pyrrole (7, Schem 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 (Schem 3), was converted into 2-formyl-3-octadeclpyrrole (14), reputed to be a metabolite of the marine sponge Oscarella lobularis. 3,4-Dibromo-1-(triisopropylsityl)pyrrole (5) was efficiently transformed, by a process involving two consecutive bromine-lithium exchange reactions (Scheme 4), into the antibiotic verrucarin E 17.