Practical total syntheses of acromelic acids A and B

…, A Asahina, T Asakawa, M Inai, Y Hamashima…

Index: Ouchi, Hitoshi; Asahina, Aya; Asakawa, Tomohiro; Inai, Makoto; Hamashima, Yoshitaka; Kan, Toshiyuki Organic Letters, 2014 , vol. 16, # 7 p. 1980 - 1983

Full Text: HTML

Citation Number: 12

Abstract

Practical total syntheses of acromelic acids A (1) and B (2), which have potent neuro- excitatory activity, were accomplished in 13 (36% total yield) and 17 steps (6.9% total yield), respectively, from 2, 6-dichloropyridine (8). Regioselective transformation of symmetric 8 provided nitroalkenes 15 and 16. The pyrrolidine ring was efficiently constructed by Ni- catalyzed asymmetric conjugate addition followed by intramolecular reductive amination.