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J-GLOBAL ID：200902291203218377   Reference number：06A0376739

Evolution of a Total Synthesis of (-)-Kendomycin Exploiting a Petasis-Ferrier Rearrangement/Ring-Closing Olefin Metathesis Strategy

Petasis-Ferrier転位/閉環オレフィンメタセシス戦略を利用した(-)-ケンドマイシンの全合成の進化

Author (3)： SMITH Amos B., III (Univ. Pennsylvania, Pennsylvania) ,  MESAROS Eugen F. (Univ. Pennsylvania, Pennsylvania) ,  MEYER Emmanuel A. (Univ. Pennsylvania, Pennsylvania)
Material： Journal of the American Chemical Society  (J Am Chem Soc)
Volume： 128  Issue： 15  Page： 5292-5299  Publication year： Apr. 19, 2006 
JST Material Number： C0254A  ISSN： 0002-7863  CODEN： JACSAT  Document type： Article
Article type： 原著論文  Country of issue： United States (USA)  Language： ENGLISH (EN)

Thesaurus term： total synthesis ,...
Semi thesaurus term： Streptomyces ,...

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JST classification (2)： Other natural substances of biological origin  (CF10090R) ,  Synthesis of antibiotics  (GX04000Z)

Substance index (20)： Kendomycin ,  2,4-Dimethoxy-3-methylbenzaldehyde ,  2,4-Dimethoxy-3-methylphenol ,  2-(tert-Butyldimethylsiloxy)-3,5-dimethoxy-4-methyl-6-bromobenzaldehyde ,  β-Citronellene ,  (2S,3R,6S)-2,6-Dimethyl-3-hydroxy-7-octenoic acid ,  (4S,6S)-2,4,6-Trimethyl-1-octene-7-yne ,  (2R)-2β-[2-Bromo-3,5-dimethoxy-4-methyl-6-(tert-butyldimethylsiloxy)phenyl]-5β-methyl-6β-[(S)-3-methyl-4-pentenyl]-1,3-dioxane-4-one ,  (2R)-2β-[2-Bromo-3,5-dimethoxy-4-methyl-6-(tert-butyldimethylsiloxy)phenyl]-4-methylene-5β-methyl-6β-[(S)-3-methyl-4-pentenyl]-1,3-dioxane ,  (2R)-2β-[2-Bromo-3,5-dimethoxy-4-methyl-6-(tert-butyldimethylsiloxy)phenyl]-5β-methyl-6β-[(S)-3-methyl-4-pentenyl]tetrahydro-2H-pyran-4-one ,  (2R)-2β-[2-Bromo-3,5-dimethoxy-4-methyl-6-(tert-butyldimethylsiloxy)phenyl]-3α,5β-dimethyl-6β-[(S)-3-methyl-4-pentenyl]tetrahydro-2H-pyran-4-one ,  (2R)-2β-[2-(tert-Butyldimethylsiloxy)-3,5-dimethoxy-4-methyl-6-bromophenyl]-3α,5β-dimethyl-4β-(tert-butyldimethylsiloxy)-6β-[(S)-3-methyl-4-pentenyl]tetrahydro-2H-pyran ,  (2R)-2β-[2-[(3S,5S)-2-Oxo-3,5,7-trimethyl-7-octenyl]-3,5-dimethoxy-4-methyl-6-(tert-butyldimethylsiloxy)phenyl]-3α,5β-dimethyl-4β-(tert-butyldimethylsiloxy)-6β-[(S)-3-methyl-4-pentenyl]tetrahydro-2H-pyran ,  (1S,17E)-1β-Hydroxy-5,10α,12β,16α,18,20β,22α-heptamethyl-4,6-dimethoxy-7,11-bis(tert-butyldimethylsiloxy)-9α,13α-epoxy-3,8-cyclocyclodocosa-3,5,7,17-tetraene ,  2-[(3S,5S)-3,5,7-Trimethyl-7-octene-1-ynyl]-3,5-dimethoxy-4-methyl-6-(tert-butyldimethylsiloxy)benzaldehyde ,  (2R)-2β-[2-[(3S,5S)-3,5,7-Trimethyl-7-octene-1-ynyl]-3,5-dimethoxy-4-methyl-6-(tert-butyldimethylsiloxy)phenyl]-5β-methyl-6β-[(S)-3-methyl-4-pentenyl]-1,3-dioxane-4-one ,  (2R)-2β-[2-[(3S,5S)-3,5,7-Trimethyl-7-octene-1-ynyl]-3,5-dimethoxy-4-methyl-6-(tert-butyldimethylsiloxy)phenyl]-4-methylene-5β-methyl-6β-[(S)-3-methyl-4-pentenyl]-1,3-dioxane ,  (2R)-2β-[2-[(3S,5S)-3,5,7-Trimethyl-7-octene-1-ynyl]-3,5-dimethoxy-4-methyl-6-(tert-butyldimethylsiloxy)phenyl]-5β-methyl-6β-[(S)-3-methyl-4-pentenyl]tetrahydro-2H-pyran-4-one ,  (9R)-5,12β,16α,18,20β,22α-Hexamethyl-4,6-dimethoxy-7-(tert-butyldimethylsiloxy)-9α,13α-epoxy-3,8-cyclocyclodocosa-3,5,7,17-tetraene-1-yne-11-one ,  (9R)-5,12β,16α,18,20β,22α-Hexamethyl-4,6-dimethoxy-7-(tert-butyldimethylsiloxy)-9α,13α-epoxy-3,8-cyclo-10-oxacyclodocosa-3,5,7,17-tetraene-1-yne-11-one

Terms in the title (7)： Ferrier転位 ,  閉環 ,  オレフィンメタセシス ,  戦略 ,  ケンドマイシン ,  全合成 ,  進化