SYNTHESIS OF PYRROLIZIDINES AND RELATED COMPOUNDS BY ALDOL CYCLIZATION OF N--α-AMINOALDEHYDES

Article abstract of DOI:10.3987/COM-87-4444

Treatment of 1-<α-(methylthio)acetyl>-2-pyrrolidinecarbaldehyde with sodium hydride in tetrahydrofuran (THF) gave the aldol condensation product, 5,6,7,7a-tetrahydro-2-methylthio-3H-pyrrolizin-3-one.However, when the same aldehyde was treated with sodium hydroxide in aqueous THF, 5,6,7,7a-tetrahydro-7a-hydroxy-3-methylthio-3H-pyrrolizin-3-one was obtained.These reactions were applied to the synthesis of indolizidine and pyrrolo<1,2-a>indole derivatives.