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Paper | Regular issue | Vol 55, No. 8, 2001, pp.1505-1518
Published online, 1st January, 1970
DOI: 10.3987/COM-01-9266
A New Asymmetric Synthesis of (R)-3-Methylpyrrolidine Alkaloids Starting from (S)-Malic Acid

Xiao Zheng, Pei Qiang Huang,* Yuan Ping Ruan, Albert W. M. Lee, and Wing Hong Chan

*Department of Chemistry, Xiamen University, Xiamen 361005, China


Diastereoselective methylation of dimethyl (S)-malate (8) followed by two three-step reductive dehydroxylation procedures afforded dimethyl (R)-2-methylsuccinate (16) in 80.2% and 84.7% ee respectively, the later was further transformed into the natural enantiomers of ant venom alkaloids (R)-leptothoracine (1) and (R)-3-methyl-N-(2-phenylethyl)pyrrolidine (2) and (3R, 2’S)-3-methyl-N-(2-methylbutyl)pyrrolidine (3).