A Short and Efficient Synthesis of Neodysiherbaine A by Using Catalytic Oxidative Cyclization

摘要

Neodysiherbaine A is an excitatory amino acid isolated from the Dysidea herbacea Micronesian sponge by Sakai et al. Biological studies have shown that (—)-neodysiherbaine A (1) is a potent convulsant and a highly selective agonist for kainate (KA) and α-amino-3-hydroxy-5-methyl-4-isoxazole propionate (AMPA) glutamate receptors.Considering its size, 1 has proven to be a challenging synthetic targetand was first synthesized by Sakai et al. in 26 steps. Since the original report, 1 has also been synthesized by Sasaki and co-workers (23 steps) and Hatakeyama and co-workers (21 steps). The most efficient synthesis reported to date was completed by Lygo et al. in 15 steps starting from diacetyl-L-arabinal. However, all of these syntheses are lengthy and involve an oxidation/reduction sequence in order to accomplish hydroxy inversion on the sugar moiety.