An expeditious synthesis of (+/-)-decahydro-5H-dipyrrolo[1,2-a : 1 ',2 '-c]pyrimidine-5-carbonitrile: a formal synthesis of (+/-)-tetraponerines-1, -2, -5, and -6

Citation
M. Plehiers et al., An expeditious synthesis of (+/-)-decahydro-5H-dipyrrolo[1,2-a : 1 ',2 '-c]pyrimidine-5-carbonitrile: a formal synthesis of (+/-)-tetraponerines-1, -2, -5, and -6, CAN J CHEM, 78(7), 2000, pp. 1030-1034
Citations number
22
Categorie Soggetti
Chemistry
Journal title
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE
ISSN journal
00084042 → ACNP
Volume
78
Issue
7
Year of publication
2000
Pages
1030 - 1034
Database
ISI
SICI code
0008-4042(200007)78:7<1030:AESO(:>2.0.ZU;2-1
Abstract
A short and practical synthesis of (+/-)-decahydro-5H-dipyrrolo[1,2-a:1',2' -c]pyrimidine-5-carbonitrile (17), a pivotal intermediate in the synthesis of (+/-)-tetraponerines-1 (5), -2 (6), -5 (7), and -6 (8), in three steps a nd 24% overall yield, from simple and inexpensive starting materials, is re ported. The key step of our synthesis is a one pot stereoselective multiste p process, whereupon two molecules of Delta(1)-pyrroline (9) react with die thyl malonate (10) to afford the tricyclic lactam ester 13, possessing the tetraponerine skeleton. Hydrolysis of the carboethoxy group of 13 followed by decarboxylation yields lactam 15, which is converted into alpha-aminonit rile 17. Our fruitless efforts to transform lactam 15 into the tetraponerin es through reductive alkylation are also discussed.