Art

J-GLOBAL ID：201702264709226203   Reference number：17A0229938

Enantioselective Total Synthesis of Mandelalide A and Isomandelalide A: Discovery of a Cytotoxic Ring-Expanded Isomer

マンデラリドAとイソマンデラリドAのエナンチオ選択性全合成:細胞毒性環拡張異性体の発見

Author (9)： VEERASAMY Nagarathanam (Oregon State Univ., Oregon, USA) ,  GHOSH Ankan (Oregon State Univ., Oregon, USA) ,  LI Jinming (Oregon State Univ., Oregon, USA) ,  WATANABE Kazuhiro (Oregon State Univ., Oregon, USA) ,  WATANABE Kazuhiro (Tohoku Pharmaceutical Univ., Sendai, JPN) ,  SERRILL Jeffrey D. (Oregon State Univ., Oregon, USA) ,  ISHMAEL Jane E. (Oregon State Univ., Oregon, USA) ,  MCPHAIL Kerry L. (Oregon State Univ., Oregon, USA) ,  CARTER Rich G. (Oregon State Univ., Oregon, USA)
Material： Journal of the American Chemical Society  (J Am Chem Soc)
Volume： 138  Issue： 3  Page： 770-773  Publication year： Jan. 27, 2016 
JST Material Number： C0254A  ISSN： 0002-7863  CODEN： JACSAT  Document type： Article
Article type： 短報  Country of issue： United States (USA)  Language： ENGLISH (EN)

Thesaurus term： total synthesis ,  molecular structure ,  *Ascidiacea ,  *lactone ,  *macrocyclic compound ,  *secondary metabolite ,  oxygen heterocyclic compound ,  silver catalyst ,  silver complex ,  catalytic reaction ,  cyclization reaction ,  dihydroxylation ,  coupling reaction ,  cytotoxicity ,  conformational transition
Semi thesaurus term： Pyrans ,  *Macrolides ,  asymmetric total synthesis

JST classification (5)： Animal biochemistry  (EJ01050P) ,  Other natural substances of biological origin  (CF10090R) ,  Eight or more-membered heterocyclic compounds  (CF07120T) ,  Aliphatic carboxylic esters,anhydrides,acid halides,acyl peroxides  (CF03210P) ,  Pharmaceutics in general  (GY01011J)

Substance index (15)： Mandelalide A ,  isomandelalide A ,  Pivalic acid ((S)-3-triethylsilyloxy-4-pentyne-1-yl) ester ,  (Z)-1-Iodo-3-((S)-2,2-dimethyl-1,3-dioxolane-4-yl)-1-propene ,  Pivalic acid ((S,Z)-3-triethylsilyloxy-8-((S)-2,2-dimethyl-1,3-dioxolane-4-yl)-6-octene-4-yne-1-yl) ester ,  Pivalic acid ((3S,6R,7S)-3-hydroxy-6,7-di(benzoyloxy)-8-((S)-2,2-dimethyl-1,3-dioxolane-4-yl)-4-octyne-1-yl) ester ,  Pivalic acid (2-((2S,5S)-3-oxo-5-((S)-1-hydroxy-2-((S)-2,2-dimethyl-1,3-dioxolane-4-yl)ethyl)tetrahydrofuran-2-yl)ethyl) ester ,  Pivalic acid (2-((2S,3S,5S)-3-methyl-5-((S)-1-(tert-butyldimethylsilyloxy)-2-((S)-2,2-dimethyl-1,3-dioxolane-4-yl)ethyl)tetrahydrofuran-2-yl)ethyl) ester ,  Triphenyl(2-((2S,3S,5S)-3-methyl-5-((S)-1-(tert-butyldimethylsilyloxy)-2-((S)-2,2-dimethyl-1,3-dioxolane-4-yl)ethyl)tetrahydrofuran-2-yl)ethyl)phosphonium ,  (R)-2-Methyl-3-((R)-oxirane-2-yl)propyl(triisopropylsilyl) ether ,  Benzoic acid ((R)-5-hexene-1-yne-3-yl) ester ,  Benzoic acid ((4R,8R,10R)-8-hydroxy-10-methyl-11-triisopropylsilyloxy-1-undecene-5-yne-4-yl) ester ,  Benzoic acid ((2S,6R)-2-allyl-6-((R)-2-methyl-3-triisopropylsilyloxypropyl)-5,6-dihydro-2H-pyran-4-yl) ester ,  (2S,6R)-2-Allyl-6-((R)-2-methyl-3-triisopropylsilyloxypropyl)-5,6-dihydro-2H-pyran-4(3H)-one ,  (R,E)-4-Methyl-5-((2R,6S)-4-(2-O-methyl-3-O,4-O-di(tert-butyldimethylsilyl)-α-L-rhamnopyranosyloxy)-6-allyl-3,4,5,6-tetrahydro-2H-pyran-2-yl)-2-pentenoic acid

Terms in the title (7)： リド ,  エナンチオ選択性 ,  全合成 ,  細胞毒性 ,  環拡張 ,  異性体 ,  発見