Art

J-GLOBAL ID：200902267196746216   Reference number：03A0186468

Iterative synthesis of the ABCDEF-ring system of yessotoxin and adriatoxin.

イェッソトキシン及びアドリアトキシンのABCDEF環系の繰返し合成

Author (3)： MORI Y (Meijo Univ., Nagoya, JPN) ,  TAKASE T (Meijo Univ., Nagoya, JPN) ,  NOYORI R (Nagoya Univ., Nagoya, JPN)
Material： Tetrahedron Letters  (Tetrahedron Lett)
Volume： 44  Issue： 11  Page： 2319-2322  Publication year： Mar. 10, 2003 
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： *oxygen heterocyclic compound ,...

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JST classification (1)： Seven-membered heterocyclic compounds  (CF07110I)

Substance index (31)： Adriatoxin ,  (2R)-2α-(tert-Butyldiphenylsiloxymethyl)-3α-(phenylsulfonyl)oxirane ,  (2S)-2β-(tert-Butyldiphenylsiloxymethyl)-3β-(phenylsulfonyl)oxirane ,  (2R)-2α-(tert-Butyldiphenylsiloxymethyl)-2-methyl-3α-(phenylsulfonyl)oxirane ,  1-O,3-O-(Di-tert-butylsilylene)-D-erythritol ,  2,2-Di-tert-butyl-4α-(trifluoromethylsulfonyloxymethyl)-5β-(triethylsiloxy)-1,3-dioxa-2-silacyclohexane ,  (2S)-2β-[2-(Benzyloxy)ethyl]-2-methyl-3β-(4-methylphenylsulfonyl)oxirane ,  (4R)-2,2-Di-tert-butyl-4α-[[(2S)-2β-[2-(benzyloxy)ethyl]-2-methyl-3-(4-methylphenylsulfonyl)oxirane-3α-yl]methyl]-5β-(triethylsiloxy)-1,3-dioxa-2-silacyclohexane ,  (1α,6β)-3,3-Di-tert-butyl-2,4,7-trioxa-8α-[2-(benzyloxy)ethyl]-8-methyl-3-silabicyclo[4.4.0]decane-9-one ,  (2S)-3α-Hydroxy-5α-(benzyloxy)-6β-[2-(benzyloxy)ethyl]-6-methyltetrahydro-2H-pyran-2β-methanol ,  Trifluoromethanesulfonic acid [(2S)-3α-(triethylsiloxy)-5α-(benzyloxy)-6β-[2-(benzyloxy)ethyl]-6-methyltetrahydro-2H-pyran-2β-yl]methyl ester ,  (2S)-2β-[[(2S)-2-(Phenylsulfonyl)-3β-(tert-butyldiphenylsiloxymethyl)oxirane-2α-yl]methyl]-3α-(triethylsiloxy)-5α-(benzyloxy)-6β-[2-(benzyloxy)ethyl]-6-methyltetrahydro-2H-pyran ,  (2S,4aβ,8aα)-2β-(tert-Butyldiphenylsiloxymethyl)-6α-[2-(benzyloxy)ethyl]-6-methyl-7β-(benzyloxy)octahydropyrano[3,2-b]pyran-3-one ,  (2S,4aβ,8aα)-2β-(Trifluoromethylsulfonyloxymethyl)-3α-(triethylsiloxy)-6α-[2-(benzyloxy)ethyl]-6-methyl-7β-(benzyloxy)octahydropyrano[3,2-b]pyran ,  (2S,4aβ,8aα)-2β-[[(2S)-2-(Phenylsulfonyl)-3β-(tert-butyldiphenylsiloxymethyl)oxirane-2α-yl]methyl]-3α-(triethylsiloxy)-6α-[2-(benzyloxy)ethyl]-6-methyl-7β-(benzyloxy)octahydropyrano[3,2-b]pyran ,  (2S,4aβ,8aα,9aα,10aβ)-2β-(tert-Butyldiphenylsiloxymethyl)-6α-(benzyloxy)-7β-[2-(benzyloxy)ethyl]-7-methyldecahydro-2H-1,8,10-trioxaanthracene-3-one ,  (2S,4aβ,8aα,9aα,10aβ)-2β-(Trifluoromethylsulfonyloxymethyl)-3α-(triethylsiloxy)-6α-(benzyloxy)-7β-[2-(benzyloxy)ethyl]-7-methyldecahydro-2H-1,8,10-trioxaanthracene ,  (2S,4aβ,8aα,9aα,10aβ)-2β-[[(2S)-2-(Phenylsulfonyl)-3β-(tert-butyldiphenylsiloxymethyl)oxirane-2α-yl]methyl]-3α-(triethylsiloxy)-6α-(benzyloxy)-7β-[2-(benzyloxy)ethyl]-7-methyldecahydro-2H-1,8,10-trioxaanthracene ,  (2S,5S,6R,8S,9R,11S,12R,14S,15R)-1-(tert-Butyldiphenylsiloxy)-14,17-bis(benzyloxy)-15-methyl-2,6:5,9:8,12:11,15-tetraepoxyheptadecane-3-one ,  (2S,3R,5S,6R,8S,9R,11S,12R,14S,15R)-1-(Trifluoromethylsulfonyloxy)-3-(triethylsiloxy)-14,17-bis(benzyloxy)-15-methyl-2,6:5,9:8,12:11,15-tetraepoxyheptadecane ,  (2R,3S,5S,6R,8S,9R,11S,12R,14S,15R,17S,18R)-1-(tert-Butyldiphenylsiloxy)-3-(phenylsulfonyl)-6-(triethylsiloxy)-17,20-bis(benzyloxy)-18-methyl-2,3:5,9:8,12:11,15:14,18-pentaepoxyicosane ,  (2S,5S,6R,8S,9R,11S,12R,14S,15R,17S,18R)-1-(tert-Butyldiphenylsiloxy)-17,20-bis(benzyloxy)-18-methyl-2,6:5,9:8,12:11,15:14,18-pentaepoxyicosane-3-one ,  (2S,6S,7R,9S,10R,12S,13R,15S,16R,18S,19R)-1-(tert-Butyldiphenylsiloxy)-18,21-bis(benzyloxy)-19-methyl-2,7:6,10:9,13:12,16:15,19-pentaepoxyhenicosane-3-one ,  Trimethylsilyldiazomethane ,  (2R,6S,7R,9S,10R,12S,13R,15S,16R,18S,19R)-1-(tert-Butyldiphenylsiloxy)-3-methylene-18,21-bis(benzyloxy)-19-methyl-2,7:6,10:9,13:12,16:15,19-pentaepoxyhenicosane ,  (2S,6S,7R,9S,10R,12S,13R,15S,16R,18S,19R)-1-(tert-Butyldiphenylsiloxy)-3,3-(oxymethylene)-18,21-bis(benzyloxy)-19-methyl-2,7:6,10:9,13:12,16:15,19-pentaepoxyhenicosane ,  (2S,3R,6S,7R,9S,10R,12S,13R,15S,16R,18S,19R)-3,19-Dimethyl-18,21-bis(benzyloxy)-2,7:6,10:9,13:12,16:15,19-pentaepoxyhenicosane-1,3-diol ,  (2S,3R,6S,7R,9S,10R,12S,13R,15S,16R,18S,19R)-1-(Trifluoromethylsulfonyloxy)-3-(trimethylsiloxy)-3,19-dimethyl-18,21-bis(benzyloxy)-2,7:6,10:9,13:12,16:15,19-pentaepoxyhenicosane ,  (2R,3S,5S,6R,9S,10R,12S,13R,15S,16R,18S,19R,21S,22R)-1-(tert-Butyldiphenylsiloxy)-2,6,22-trimethyl-3-(4-methylphenylsulfonyl)-6-(trimethylsiloxy)-21,24-bis(benzyloxy)-2,3:5,10:9,13:12,16:15,19:18,22-hexaepoxytetracosane ,  (2S,5S,6R,9S,10R,12S,13R,15S,16R,18S,19R,21S,22R)-1-(tert-Butyldiphenylsiloxy)-2,6,22-trimethyl-21,24-bis(benzyloxy)-2,6:5,10:9,13:12,16:15,19:18,22-hexaepoxytetracosane-3-one ,  (2S,3R,5S,6R,9S,10R,12S,13R,15S,16R,18S,19R,21S,22R)-2,6,22-Trimethyl-21,24-bis(benzyloxy)-2,6:5,10:9,13:12,16:15,19:18,22-hexaepoxytetracosane-1,3-diol

Terms in the title (2)： アドリアトキシン ,  環