Synthesis of (±)-trans-2,5-Dialkylpyrrolidines from the Lukes-Šorm Dilactam: Efficient Preparation of (±)-trans-2-Butyl-5-heptylpyrrolidine and Analogs Present in Ant Venoms
✍ Scribed by Wieslaw Gessner; Kimio Takahashi; Arnold Brossi; Marek Kowalski; Michael A. Kaliner
- Publisher
- John Wiley and Sons
- Year
- 1987
- Tongue
- German
- Weight
- 580 KB
- Volume
- 70
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
A 7-step synthesis of (*)-trans-2-butyl-5-heptylpyrrolidine (14) from the Lukes-Sorm dilactam 1 was accomplished in 6 % overall yield without counting for a reconversion of cis-isomer 13 into trans-isomer 14 which was also accomplished. Reduction of pyrroline 12, the precursor of 14, with NaBH, afforded a 1:l mixture of cis-isomer 13 and trans-isomer 14 separated by chromatography. Reductive N-methylation of 14 afforded the N-methyl analog 15, another ant alkaloid. The synthetic route to 14 was extended to a similar synthesis of analogs 23-25 and is representative for the synthesis of trans-2,5-diakyl-substituted pyrrolidines. Results on the screening of a few compounds for the effect on vascular permeability are reported.