A stereocontrolled organopalladium route to 2, 5-disubstituted pyrrolidine derivatives. Application to the synthesis of a venom alkaloid of the ant species Monomorium …

JE Baeckvall, HE Schink, ZD Renko

Index: Baeckvall, Jan-E.; Schink, Hans E.; Renko, Z. Dolor Journal of Organic Chemistry, 1990 , vol. 55, # 3 p. 826 - 831

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Citation Number: 58

Abstract

A general method for the preparation of cis-and trans-2, 5-disubstituted pyrrolidines from conjugated dienes has been developed. The approach involves a stereocontrolled syn-or anti-1, Caddition of an amino and an oxygen function to the diene via palladium catalysis. Subsequent stereospecific cyclization produces the pure cis-and trans-2, 5-disubstituted pyrrolidines, respectively. The method was applied to the synthesis of an ant venom ...