Abstract
N-BOC-ethyl pyroglutamate 1 undergoes nucleophilic ring opening with lithium methyl p-tolyl sulfinyl anion delivering the p-tolylketosulfoxide 2. Treatment of 2 with TFA gave rise to a mixture of thioesters 3a,3b. The hydrolysis of 3b afforded (2S, 5S) pirrolidine-2,5 dicarboxylic acid 5, a constituent of the red Alga Schizymenia dubyi . Under Pummerer reaction conditions (TFAA/Pyr), 2 yielded the 5-oxo-L-pipecolic acid derivative 6.
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