Practical Synthesis of PGI2 Agonist: Resolution–Inversion–Recycle Approach of Its Chiral Intermediate

…, A Kanda, S Moriki, Y Baba, N Hashimoto…

Index: Ohigashi, Atsushi; Kanda, Atsushi; Moriki, Shigeru; Baba, Yukihisa; Hashimoto, Norio; Okada, Minoru Organic Process Research and Development, 2013 , vol. 17, # 4 p. 658 - 665

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Abstract

Practical synthesis of ((2 R)-5-benzyloxy-2-hydroxy-1, 2, 3, 4-tetrahydronaphth-2-yl) methanol ((R)-7b), a key chiral intermediate for the synthesis of the novel PGI2 agonist,(R)-[6- [(diphenylcarbamoyloxy) methyl]-6-hydroxy-5, 6, 7, 8-tetrahydronaphthalen-1-yloxy] acetic acid (1), was achieved via optical resolution by diastereoselective crystallization of ester derivative 18 of racemic (5-benzyloxy-2-hydroxy-1, 2, 3, 4-tetrahydronaphth-2-yl) ...