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| Finally, all library members were cleaved from the solid support using HF•pyridine (pyridine, THF, 50 ¡ãC) and purified by preparative reverse-phase HPLC to afford the final library of 190 alkaloid/terpenoid-like compounds (both enantiomeric series), comprised of 18 cyclopentapyrrolidinones (11¨C13), 30 exo-pyrrolines (14¨C19), 6 cyclooctapyrrolidines (20), 18 vinylpyrrolines (21¨C23), 6 benzodipyrrolidines (24), and 6 isoindoline dicarboxylates (25) derived from the enyne substrates and 28 isoindoline alcohols (30¨C38), 24 pyrrolopyridones (36¨C41), 18 pyrrolopyridine carboxylates (42¨C44), and 36 cycloheptapyrrolidine amides (45¨C50) derived from the diyne substrates. The products were isolated in 20.2% average yield over 5¨C8 solid-phase steps, at 74.0% average yield per step (SI Appendix, Table S1). |
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