Practical Total Syntheses of Acromelic Acids A and B
journal contributionposted on 04.04.2014, 00:00 by Hitoshi Ouchi, Aya Asahina, Tomohiro Asakawa, Makoto Inai, Yoshitaka Hamashima, Toshiyuki Kan
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.