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J-GLOBAL ID：201602250106489337   Reference number：16A0713447

Convenient synthesis of (+)-cis-4-(N-adamantyl-N-methylamino)-2,3-methano-2-phenylbutan-1-ol as a candidate of anti-Alzheimer’s medicine via catalytic enantioselective Simmons-Smith reaction using l-phenylalanine-derived disulfonamide

L-フェニルアラニンから誘導体したジスルホンアミドを用いた,接触的エナンチオ選択的Simmons-Smith反応を経由する,Alzheimer病治療薬候補としての(+)-cis-4-(N-アダマンチル-N-メチルアミノ)-2,3-メタノ-2-フェニルブタン-1-オールの便利な合成

Author (6)： Kawashima Yuya (Faculty of Pharmacy, Chiba Institute of Science, 15-8 Shiomi-cho, Choshi, Chiba 288-0025, Japan) ,  Ezawa Tetsuya (Faculty of Pharmacy, Chiba Institute of Science, 15-8 Shiomi-cho, Choshi, Chiba 288-0025, Japan) ,  Yamamura Mai (Faculty of Pharmacy, Chiba Institute of Science, 15-8 Shiomi-cho, Choshi, Chiba 288-0025, Japan) ,  Harada Taisuke (Faculty of Pharmacy, Chiba Institute of Science, 15-8 Shiomi-cho, Choshi, Chiba 288-0025, Japan) ,  Noguchi Takuya (Faculty of Pharmacy, Chiba Institute of Science, 15-8 Shiomi-cho, Choshi, Chiba 288-0025, Japan) ,  Imai Nobuyuki (Faculty of Pharmacy, Chiba Institute of Science, 15-8 Shiomi-cho, Choshi, Chiba 288-0025, Japan)
Material： Tetrahedron Letters  (Tetrahedron Lett)
Volume： 57  Issue： 6  Page： 668-671  Publication year： Feb. 10, 2016 
JST Material Number： E0366A  ISSN： 0040-4039  Document type： Article
Article type： 短報  Country of issue： United Kingdom (GBR)  Language： ENGLISH (EN)

Thesaurus term： asymmetric synthesis ,  *anti-Alzheimer's disease drug ,  *alicyclic compound ,  *alcohol ,  tertiary amine ,  acetylation ,  cycloaddition ,  amidation ,  bridged compound ,  aromatic compound
Semi thesaurus term： Simmons-Smith reaction ,  Cyclopropanes ,  primary alcohol

Author keywords (5)： Alzheimer’s disease ,  Sigma receptor agonist ,  Regioselective acetylation ,  Simmons-Smith reaction ,  Amidation

JST classification (2)： Cyclopropanes  (CF04020P) ,  Basic research of other drugs acting on central nervous system  (GW03120U)

Substance index (11)： (Z)-2-Phenyl-2-butene-1,4-diol ,  (Z)-2-Phenyl-2-butene-1,4-diol 4-acetate ,  (Z)-3-Phenyl-4-[(tert-butyldiphenylsilyl)oxy]-2-butene-1-ol ,  (2S)-N-Tosyl-N′-mesyl-3-phenyl-1,2-propanediamine ,  rel-1-Phenyl-2α^*-[(1-adamantylamino)methyl]cyclopropane-1α^*-methanol ,  rel-1-Phenyl-2α^*-[[methyl(1-adamantyl)amino]methyl]cyclopropane-1α^*-methanol ,  rel-2α^*-[(tert-Butyldiphenylsilyloxy)methyl]-2-phenylcyclopropane-1α^*-carbaldehyde ,  rel-2α^*-[(tert-Butyldiphenylsilyloxy)methyl]-2-phenylcyclopropane-1α^*-carboxylic acid ,  rel-2α^*-[(tert-Butyldiphenylsilyloxy)methyl]-2-phenylcyclopropane-1α^*-methanol ,  rel-N-(1-Adamantyl)-2α^*-[(tert-butyldiphenylsilyloxy)methyl]-2-phenylcyclopropane-1α^*-carboxamide ,  Acetic acid (Z)-3-phenyl-4-[(tert-butyldiphenylsilyl)oxy]-2-butenyl ester

Terms in the title (6)： L-フェニルアラニン ,  誘導体 ,  Simmons-Smith反応 ,  Alzheimer病治療薬 ,  CIS ,  2-フェニルブタン