Art

J-GLOBAL ID：200902160449793888   Reference number：97A0898460

Synthesis of 1-Hydroxybicyclo[3.2.1]oct-3-en-2-ones by Acyloin Rearrangement of 1-Methoxy- or 1-tert-Butyldimethylsilyloxy-bicyclo[2.2.2]oct-5-en-2-ones.

1-メトキシ-又は1-t-ブチルジメチルシリルオキシ-ビシクロ[2.2.2]オクタ-5-エン-2-オン類のアシロイン転位による1-ヒドロキシビシクロ[3.2.1]オクタ-3-エン-2-オン類の合成

Author (4)： KATAYAMA S (Josai Univ., Saitama, JPN) ,  HIRAMATSU H (Tanabe Seiyaku Co., Ltd., Osaka, JPN) ,  AOE K (Tanabe Seiyaku Co., Ltd., Osaka, JPN) ,  YAMAUCHI M (Josai Univ., Saitama, JPN)
Material： Chemical and Pharmaceutical Bulletin  (Chemical & Pharmaceutical Bulletin)
Volume： 45  Issue： 9  Page： 1419-1427  Publication year： Sep. 1997 
JST Material Number： G0504A  ISSN： 0009-2363  CODEN： CPBTAL  Document type： Article
Article type： 原著論文  Country of issue： Japan (JPN)  Language： ENGLISH (EN)

Thesaurus term： chemical synthesis ,...
Semi thesaurus term： bridged compound ,...

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JST classification (2)： Bridged tri-or more-cyclic carbocyclic compounds  (CF06110B) ,  Rearrangement reaction,isomerization  (CF02070E)

Substance index (17)： (1R)-1,3,5,7-Tetramethoxy-3α,5β-bis(methylthiomethyl)-1,3,4,4aβ,5,8aβ-hexahydro-1α,4α-ethenonaphthalene-2,6-dione ,  (4R)-2α,4-Dimethoxy-2-(methylthiomethyl)-1,2,4aα,9aα-tetrahydro-1β,4-etheno-9H-fluoren-3(4H)-one ,  (4bR,11S)-5-Hydroxy-11-methoxy-11-(methylthiomethyl)-4bβ,9,9aβ,10-tetrahydro-5β,9β-methanobenz[a]azulen-6(5H)-one ,  (3aS,9S)-4-Hydroxy-9-methoxy-9-(methylthiomethyl)-1,3aβ,8,8aβ-tetrahydro-4β,8β-methanoazulen-5(4H)-one ,  (3aS,9S)-1,1-Dimethyl-4-hydroxy-9-methoxy-9-(methylthiomethyl)-1,3aβ,8,8aβ-tetrahydro-4β,8β-methanoazulen-5(4H)-one ,  (1R,2S,5S,6R)-3-Methyl-6-hydroxy-10-methoxy-10-(methylthiomethyl)tricyclo[4.3.1.0^2,5]deca-3,8-dien-7-one ,  (1R,5β,8S)-1α-Hydroxy-7α-acetyl-8-methoxy-8-(methylthiomethyl)bicyclo[3.2.1]oct-3-en-2-one ,  (1R,5β,8S)-1α-Hydroxy-7α-propionyl-8-methoxy-8-(methylthiomethyl)bicyclo[3.2.1]oct-3-en-2-one ,  (1R,5β,8S)-1α-Hydroxy-7α-formyl-8-methoxy-8-(methylthiomethyl)bicyclo[3.2.1]oct-3-en-2-one ,  (1R)-2β-(Methylthiomethyl)-2,4-bis(tert-butyldimethylsiloxy)-1,4,4aα,9aα-tetrahydro-1β,4β-etheno-9H-fluoren-3(2H)-one ,  (3aS)-4,6-Bis(tert-butyldimethylsiloxy)-6α-(methylthiomethyl)-1,3aβ,4,6,7,7aβ-hexahydro-4α,7α-etheno-5H-inden-5-one ,  (3aS)-1,1-Dimethyl-4,6-bis(tert-butyldimethylsiloxy)-6α-(methylthiomethyl)-1,3aβ,4,6,7,7aβ-hexahydro-4α,7α-etheno-5H-inden-5-one ,  (1R,3S,4S,7R)-1,3β-Bis(tert-butyldimethylsiloxy)-3-(methylthiomethyl)-7-acetylbicyclo[2.2.2]oct-5-en-2-one ,  (1R,3S,4S,7R)-1,3β-Bis(tert-butyldimethylsiloxy)-3-(methylthiomethyl)-7-formylbicyclo[2.2.2]oct-5-en-2-one ,  (1R,3S,4S)-1,3β-Bis(tert-butyldimethylsiloxy)-2-oxo-3-(methylthiomethyl)bicyclo[2.2.2]oct-5-ene-7β-carboxylic acid methyl ester ,  (1R,3S,4S)-1,3β-Bis(tert-butyldimethylsiloxy)-2-oxo-3-(methylthiomethyl)bicyclo[2.2.2]oct-5-ene-7β-carboxylic acid tert-butyl ester ,  (1R,3S,4S)-1,3β-Bis(tert-butyldimethylsiloxy)-2-oxo-3-(methylthiomethyl)bicyclo[2.2.2]oct-5-ene-7β-carbonitrile

Reference (18)：

• COLLINS, C. J. The Chemistry of the Carbonyl Group. 1966, 761-821
• POCKER, Y. Molecular Rearrangements. 1963, 1, 1-25
• PCCKER, Y. Molecular Rearrangements. 2, 771-834
• WENDLER, N. L. Molecular Rearrangements. 1963, 2, 917, 1019-1138
• GRUNEWALD, G. L. J.Org.Chem. 1978, 43, 3478-3481

Terms in the title (2)： アシロイン ,  転位