Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact: purchase@heterocycles.com

Price: ¥ 4,320 (Yen only)
Period: This Article can be accessed for 7 days.

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

Abstract

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).