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Paper | Regular issue | Vol 27, No. 4, 1988, pp.943-953
Published online, 1st January, 1970
DOI: 10.3987/COM-87-4444
Synthesis of Pyrrolizidines and Related Compounds by Aldol Cyclization of N-[α-(Methylthio)acetyl]-α-aminoaldehydes

Masazumi Ikeda,* Suzumi Harada, Atsuko Yamasaki, Katsuko Kinouchi, and Hiroyuki Ishibashi

*Kyoto Pharmaceutical University, Misasagi-Shichonocho, Yamashina, Kyoto 607-8414, Japan


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-methylthlo-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.