86630-10-6Relevant articles and documents
Practical total syntheses of acromelic acids A and B
Inai, Makoto,Ouchi, Hitoshi,Asahina, Aya,Asakawa, Tomohiro,Hamashima, Yoshitaka,Kan, Toshiyuki
, p. 723 - 732 (2016/07/19)
Practical total syntheses of acromelic acids A (1) and B (2), which were scarce natural products isolated from toxic mushroom by Shirahama and Matsumoto, were accomplished in 13 (36% total yield) and 17 steps (6.9% total yield), respectively, from 2,6-dichloropyridine (8). Beginning with regioselective transformation of symmetric 8 by either ortho-lithiation or bromination, nitroalkenes 15 and 16 were provided. Stereoselective construction of the vicinal stereocenters at the C-3, 4 positions of 1 and 2 was performed by a Ni-catalyzed asymmetric conjugate addition of α-ketoesters to the nitroalkenes. Construction of the pyrrolidine ring was accomplished in a single operation via a sequence consisting of reduction of the nitro group, intramolecular condensation with the ketone, and reduction of the resulting ketimine.
Efficient Syntheses of Acromelic Acids B and E, Which Are Potent Neuroexcitatory Amino Acids
Horikawa, Manabu,Hashimoto, Kimiko,Shirahama, Haruhisa
, p. 331 - 334 (2007/10/02)
(-)-Acromelic acid B (2) was synthesized from 2-cyano-3-(2-hydroxyethyl)pyridine (4) in 21percent overall yield.Acromelic acid E (3) was also prepared on the way of above synthesis.
Synthesis of Acromelic Acid B, a Toxic Principle of Clitocybe acromelalga
Hashimoto, Kimiko,Konno, Katsuhiro,Shirahama, Haruhisa,Matsumoto, Takeshi
, p. 1399 - 1400 (2007/10/02)
Acromelic acid B was synthesized from kainic acid through our newly developed method of pyridine synthesis.
