Art

J-GLOBAL ID：201102265226014610   Reference number：11A1056114

Asymmetric synthesis of (-)-chicanine using a highly regioselective intramolecular Mitsunobu reaction and revision of its absolute configuration

高度位置選択的分子内Mitsunobu反応を使用する(-)-キカニンの不斉合成およびその絶対配置の修正

Author (8)： HARADA Kenichi (Fac. of Pharmaceutical Sciences, Tokushima Bunri Univ., Yamashiro-cho, Tokushima 770-8514, JPN) ,  HORIUCHI Hiroki (Fac. of Pharmaceutical Sciences, Tokushima Bunri Univ., Yamashiro-cho, Tokushima 770-8514, JPN) ,  TANABE Kazuma (Fac. of Pharmaceutical Sciences, Tokushima Bunri Univ., Yamashiro-cho, Tokushima 770-8514, JPN) ,  CARTER Rich G. (Dep. of Chemistry, Oregon State Univ., Gilbert Hall, Corrvallis, OR 97331, USA) ,  ESUMI Tomoyuki (Fac. of Pharmaceutical Sciences, Tokushima Bunri Univ., Yamashiro-cho, Tokushima 770-8514, JPN) ,  KUBO Miwa (Fac. of Pharmaceutical Sciences, Tokushima Bunri Univ., Yamashiro-cho, Tokushima 770-8514, JPN) ,  HIOKI Hideaki (Fac. of Education, Gunma Univ., Maebashi, Gunma 371-8510, JPN) ,  FUKUYAMA Yoshiyasu (Fac. of Pharmaceutical Sciences, Tokushima Bunri Univ., Yamashiro-cho, Tokushima 770-8514, JPN)
Material： Tetrahedron Letters  (Tetrahedron Lett)
Volume： 52  Issue： 23  Page： 3005-3008  Publication year： Jun. 08, 2011 
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： regiospecific reaction ,  *Mitsunobu reaction ,  *asymmetric synthesis ,  hydroboration ,  *absolute configuration ,  aldol reaction ,  *oxygen heterocyclic compound ,  polynuclear aromatic compound ,  phenol ether
Semi thesaurus term： *Benzodioxoles

JST classification (1)： Dioxoles,oxathioles,dithioles  (CF07079K)

Substance index (14)： Chicanin ,  (-)-Chicanine ,  Talaumidin ,  (1S,2R,3S,4R)-1-[3-Methoxy-4-(benzyloxy)phenyl]-2,3-dimethyl-4-(1,3-benzodioxole-5-yl)butane-1,4-diol ,  (2S,3R,4S)-2,3-Dimethyl-4-[3-methoxy-4-(benzyloxy)phenyl]-4-(tert-butyldimethylsilyloxy)-1-butanol ,  (3R,4S)-2,3-Dimethyl-4-[3-methoxy-4-(benzyloxy)phenyl]-4-(tert-butyldimethylsilyloxy)-1-butene ,  4-Benzyloxy-3-methoxybenzaldehyde ,  (3R,4S)-3-Methyl-4-(tert-butyldimethylsilyloxy)-4-[3-methoxy-4-(benzyloxy)phenyl]-2-butanol ,  (1S,2R,3S,4R)-1-[3-Methoxy-4-(tosyloxy)phenyl]-2,3-dimethyl-4-(1,3-benzodioxole-5-yl)butane-1,4-diol ,  2α-(1,3-Benzodioxole-5-yl)-3β,4β-dimethyl-5β-[3-methoxy-4-(benzyloxy)phenyl]tetrahydrofuran ,  2β-(1,3-Benzodioxole-5-yl)-3β,4β-dimethyl-5α-[3-methoxy-4-(benzyloxy)phenyl]tetrahydrofuran ,  Benzoic acid 2-methoxy-4-[(2S)-3α,4α-dimethyl-5β-(1,3-benzodioxole-5-yl)tetrahydrofuran-2α-yl]phenyl ester ,  p-Toluenesulfonic acid 2-methoxy-4-[(2S)-3α,4α-dimethyl-5β-(1,3-benzodioxole-5-yl)tetrahydrofuran-2α-yl]phenyl ester ,  (1R,2S,3R,4S)-1-(1,3-Benzodioxole-5-yl)-2,3-dimethyl-4-(tert-butyldimethylsilyloxy)-4-[3-methoxy-4-(benzyloxy)phenyl]butane-1-ol

Terms in the title (4)： 高度 ,  位置選択 ,  Mitsunobu反応 ,  不斉合成