692730-97-5Relevant articles and documents
Convenient synthesis of memantine analogues containing a chiral cyclopropane skeleton as a sigma-1 receptor agonist
Ezawa, Tetsuya,Kawashima, Yuya,Noguchi, Takuya,Jung, Seunghee,Imai, Nobuyuki
, p. 266 - 281 (2017/02/18)
We have achieved a convenient enantioselective synthesis of memantine analogues containing a chiral cyclopropane skeleton as a sigma-1 receptor agonist in 19–40% overall chemical yields from the corresponding 2-arylbut-2-ene-1,4-diols with moderate to excellent asymmetric yields via regioselective acetylation using porcine pancreas lipase, catalytic enantioselective Simmons-Smith reactions, and amidation in aqueous organic solvent. This synthetic route is more efficient and less expensive than conventional methods.
Asymmetric syntheses of pharmaceuticals containing a cyclopropane moiety using catalytic asymmetric Simmons-Smith reactions of allylalcohols: Syntheses of optically active tranylcypromine and milnacipran
Ishizuka, Yuki,Fujimori, Hirohisa,Noguchi, Takuya,Kawasaki, Masashi,Kishida, Mari,Nagai, Takuya,Imai, Nobuyuki,Kirihara, Masayuki
, p. 1311 - 1313 (2013/10/22)
Asymmetric synthesis of tranylcypromine was achieved using an enantioselective Simmons-Smith cyclopropanation catalyzed by a simple disulfonamide derived from an -amino acid. The optically active milnacipran was also synthesized by porcine pancreas lipase-catalyzed selective monoacylation of the C4-hydroxy group in (Z)-2-phenylbut-2-ene-1,4-diol and the enantioselective Simmons-Smith cyclopropanation as the key steps.
