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Paper | Regular issue | Vol 43, No. 4, 1996, pp.755-766
Published online, 1st January, 1970
DOI: 10.3987/COM-95-7293
Enantioselective Total Synthesis of Irniine and Bgugaine, Bioactive 2-Alkylpyrrolidine Alkaloids

Akino Jossang,* Ahmed Melhaoui, and Bernard Bodo

*Laboratoire de Chimie des Substances Naturelles, Muséum National d'Histoire Naturelle, URA 401 CNRS, 63 rue Buffon 75005 Paris, France

Abstract

An asymmetric total synthesis of the 2-(R)-alkylpyrrolidines, (-)-irniine (1a) and (-)-bgugaine (1b), toxic and antibiotic component of the tubers of Arisarum vulgare, and (+)-(S)-irniine (1c), was carried out by condensation of the corresponding 4-oxoalkanoic acid (9) with chiral phenylglycinol. Acids (9) were prepared from a hetero-organocuprate (I) complex, generated by reaction of methylcopper (I) with alkylmagnesium bromides and methyl chlorocarbonylpropionate. Alkaloids (1a, 1b and 1c) displayed anti Gram(+) bacterial (MIC 12.5 - 50 μg/ml) and antifungal (MIC 6.25 - 50 μg/ml) activities.