Total synthesis of dysiherbaine |
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Authors: | Makoto Sasaki Nobuyuki Akiyama Muneo Shoji Ryuichi Sakai |
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Institution: | a Laboratory of Biostructural Chemistry, Graduate School of Life Sciences, Tohoku University, Sendai 981-8555, Japan b School of Fisheries Sciences, Kitasato University, Sanriku-cho, Iwate 022-0101, Japan |
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Abstract: | An efficient total synthesis of dysiherbaine, a potent and subtype-selective agonist for ionotropic glutamate receptors, has been achieved. An advanced key intermediate in the previous synthesis of neodysiherbaine A and its analogues was selected as the starting point, and cis-oriented amino alcohol functionality on the tetrahydropyran ring was installed by using an intramolecular SN2 cyclization of N-Boc-protected amino alcohol. The amino acid appendage was constructed by catalytic asymmetric hydrogenation of enamide ester. |
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