ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
A 7-step synthesis of (±)-trans-2-butyl-5-heptylpyrrolidine (14) from the Lukes-Šorm 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 NaBH4 afforded a 1:1 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.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19870700805
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