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Communication | Special issue | Vol 50, No. 1, 1999, pp.31-34
Published online, 1st January, 1970
DOI: 10.3987/COM-98-S(H)13
A Synthesis of (±)-Ipalbidine Using Sulfur-controlled 6-Exo Selective Radical Cyclization of α-Phenylthio Amide

Masazumi Ikeda,* Jiro Shikaura, Noriko Maekawa, Kaori Daibuzono, Hirotaka Teranishi, Yoshiko Teraoka, Norio Oda, and Hiroyuki Ishibashi*

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


A synthesis of (±)-ipalbidine (1) has been achieved using Bu3SnH-mediated 6-exo selective radical cyclization of 2-[3-(phenylthio)prop-2-enyl]-N-[α-(p-methoxyphenyl)-α-(phenylthio)acetyl]pyrrolidine (15) as a key step.