Art

J-GLOBAL ID：200902262288326076   Reference number：08A0690381

Total Synthesis of (-)-Martinellic Acid via Radical Addition-Cyclization-Elimination Reaction

ラジカル付加-環化-脱離反応による(-)-マルチネリン酸の全合成

Author (7)： SHIRAI Atsushi (Kobe Pharmaceutical Univ., Kobe, JPN) ,  MIYATA Okiko (Kobe Pharmaceutical Univ., Kobe, JPN) ,  TOHNAI Norimitsu (Osaka Univ., Osaka, JPN) ,  MIYATA Mikiji (Osaka Univ., Osaka, JPN) ,  PROCTER David J. (Univ. Manchester, Manchester, GBR) ,  SUCUNZA David (Univ. Manchester, Manchester, GBR) ,  NAITO Takeaki (Kobe Pharmaceutical Univ., Kobe, JPN)
Material： Journal of Organic Chemistry  (J Org Chem)
Volume： 73  Issue： 12  Page： 4464-4475  Publication year： Jun. 20, 2008 
JST Material Number： C0328A  ISSN： 0022-3263  CODEN： JOCEAH  Document type： Article
Article type： 原著論文  Country of issue： United States (USA)  Language： ENGLISH (EN)

Thesaurus term： total synthesis ,  radical reaction ,  cyclization reaction ,  elimination reaction ,  asymmetric synthesis ,  Mitsunobu reaction ,  *quinoline alkaloid ,  oxime ether ,  optical activity ,  reduction (reaction) ,  samarium compound ,  iodide ,  addition reaction ,  aliphatic compound ,  organotin compound ,  samarium diiodide
Semi thesaurus term： *ピロロキノリンアルカロイド

JST classification (1)： Alkaloids  (CF10030D)

Substance index (24)： Tributyltin ,  Martinellic acid ,  (3aS)-4β-[3-(tert-Butyldimethylsilyloxy)propyl]-5-tosyl-2,3,3aβ,4,5,9bα-hexahydro-1H-pyrrolo[3,2-c]quinoline-2-one ,  (3aR)-4α-[3-(tert-Butyldimethylsilyloxy)propyl]-5-tosyl-2,3,3aα,4,5,9bα-hexahydro-1H-pyrrolo[3,2-c]quinoline-2-one ,  3-Methyl-4-bromobenzoic acid methyl ester ,  (2S)-1-[2-[(Benzyloxyimino)methyl]phenyl]-5-oxopyrrolidine-2-carboxylic acid ethyl ester ,  (2S)-1-[2-[(Benzyloxyimino)methyl]-4-(methoxycarbonyl)phenyl]-5-oxopyrrolidine-2-carboxylic acid ethyl ester ,  (E)-3-[(2S)-1-[2-[(Benzyloxyimino)methyl]phenyl]-5-oxo-2-pyrrolidinyl]propenoic acid ethyl ester ,  (E)-3-[(2S)-1-[4-(Methoxycarbonyl)-2-(benzyloxyiminomethyl)phenyl]-5-oxopyrrolidine-2-yl]acrylic acid ethyl ester ,  (3aS,3bS,11bS)-2,3,3a,3b,4,5,6,11b-Octahydro-1H-dipyrrolo[1,2-a:3′,2′-c]quinoline-2,6-dione ,  (3aS,3bS,11bS)-2,6-Dioxo-2,3,3a,3b,4,5,6,11b-octahydro-1H-dipyrrolo[1,2-a:3′,2′-c]quinoline-10-carboxylic acid methyl ester ,  (3aS)-4α-[3-(tert-Butyldimethylsilyloxy)propyl]-2,3,3aα,4,5,9bα-hexahydro-1H-pyrrolo[3,2-c]quinoline-2-one ,  (3aS)-2-Oxo-4α-(3-hydroxypropyl)-2,3,3aα,4,5,9bα-hexahydro-1H-pyrrolo[3,2-c]quinoline-8-carboxylic acid methyl ester ,  (3aS)-4α-(3-Hydroxypropyl)-2,3,3aα,4,5,9bα-hexahydro-1H-pyrrolo[3,2-c]quinoline-8-carboxylic acid methyl ester ,  (3aS)-1,5-Bis(trifluoroacetyl)-4α-(3-hydroxypropyl)-2,3,3aα,4,5,9bα-hexahydro-1H-pyrrolo[3,2-c]quinoline-8-carboxylic acid methyl ester ,  (3aS)-1,5-Bis(2,2,2-trichloroethoxycarbonyl)-4α-(3-hydroxypropyl)-2,3,3aα,4,5,9bα-hexahydro-1H-pyrrolo[3,2-c]quinoline-8-carboxylic acid methyl ester ,  1,3-Bis(tert-butoxycarbonyl)-2-methylisothiourea ,  (3aS)-1,5-Bis(trifluoroacetyl)-4α-[3-[1,3-bis(tert-butyloxycarbonyl)-2-methyl-1-isothioureido]propyl]-2,3,3aα,4,5,9bα-hexahydro-1H-pyrrolo[3,2-c]quinoline-8-carboxylic acid methyl ester ,  (3aS)-1,5-Bis(2,2,2-trichloroethoxycarbonyl)-4α-[3-[1,3-bis(tert-butyloxycarbonyl)-2-methyl-1-isothioureido]propyl]-2,3,3aα,4,5,9bα-hexahydro-1H-pyrrolo[3,2-c]quinoline-8-carboxylic acid methyl ester ,  (3aS)-1,5-Bis(trifluoroacetyl)-4α-[3-[1,2-bis(tert-butyloxycarbonyl)-3-(3-methyl-2-butenyl)guanidino]propyl]-2,3,3aα,4,5,9bα-hexahydro-1H-pyrrolo[3,2-c]quinoline-8-carboxylic acid methyl ester ,  (3aS)-1,5-Bis(2,2,2-trichloroethoxycarbonyl)-4α-[3-[1,2-bis(tert-butyloxycarbonyl)-3-(3-methyl-2-butenyl)guanidino]propyl]-2,3,3aα,4,5,9bα-hexahydro-1H-pyrrolo[3,2-c]quinoline-8-carboxylic acid methyl ester ,  1-Prenyl-2-methyl-3-(tert-butoxycarbonyl)isothiourea ,  (3aS)-1-[(3-Methyl-2-butenylamino)(tert-butyloxycarbonylimino)methyl]-4α-[3-[2-(tert-butyloxycarbonyl)-3-(3-methyl-2-butenyl)guanidino]propyl]-2,3,3aα,4,5,9bα-hexahydro-1H-pyrrolo[3,2-c]quinoline-8-carboxylic acid methyl ester ,  (3aS)-1-[(3-Methyl-2-butenylamino)(tert-butyloxycarbonylimino)methyl]-4α-[3-[1,2-bis(tert-butyloxycarbonyl)-3-(3-methyl-2-butenyl)guanidino]propyl]-2,3,3aα,4,5,9bα-hexahydro-1H-pyrrolo[3,2-c]quinoline-8-carboxylic acid methyl ester

Terms in the title (5)： ラジカル付加 ,  環化 ,  脱離反応 ,  マルチネリン酸 ,  全合成