Art

J-GLOBAL ID：201202229452358462   Reference number：12A0776673

A Synthetic Approach to Diverse 3-Acyltetramic Acids via O- to C-Acyl Rearrangement and Application to the Total Synthesis of Penicillenol Series

O-からC-へのアシル転位を介したさまざまな3-アシルテトラム酸への合成アプローチおよびペニシレノールシリーズ全合成への応用

Author (5)： SENGOKU Tetsuya (Shizuoka Univ., Shizuoka, JPN) ,  NAGAE Yuta (Shizuoka Univ., Shizuoka, JPN) ,  UJIHARA Yasuaki (Shizuoka Univ., Shizuoka, JPN) ,  TAKAHASHI Masaki (Shizuoka Univ., Shizuoka, JPN) ,  YODA Hidemi (Shizuoka Univ., Shizuoka, JPN)
Material： Journal of Organic Chemistry  (J Org Chem)
Volume： 77  Issue： 9  Page： 4391-4401  Publication year： May. 04, 2012 
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： nitrogen heterocyclic compound ,  carbonyl compound ,  *Acylation ,  *rearrangement reaction ,  additive effect ,  molecular structure ,  chemical synthesis ,  Penicillins ,  functional group protection ,  enol ,  enone ,  Calcium Chloride ,  fatty acid ,  steroid ,  conjugated diene ,  alicyclic ketone ,  carboxylate (ester) ,  diketone ,  hydroxy ketone ,  amino acid ,  aliphatic amine ,  aliphatic alcohol ,  aliphatic carboxylic acid ,  primary amine ,  alpha-amino acid ,  Dieckmann condensation ,  *Pyrrolidines ,  antibacterial drug ,  antimicrobial drug ,  drug
Semi thesaurus term： Dieckmann condensation reaction ,  *dione ,  *Pyrrolidines

JST classification (2)： Pyrroles  (CF07076L) ,  Synthesis of antibiotics  (GX04000Z)

Substance index (23)： Acetic acid megestrol ,  2,2-Dimethyl-1,3-dioxane-4,6-dione ,  (S)-2-Methyloctanoic acid (2S)-2β-[(R)-1-(tert-butyldimethylsiloxy)ethyl]-5-oxo-3-pyrroline-3-yl ester ,  (5S)-3-[(Z)-1-Hydroxy-2-methyloctylidene]-5α-[(R)-1-(tert-butyldimethylsiloxy)ethyl]pyrrolidine-2,4-dione ,  Penicillenol A₁ ,  Boc-Phenylalanine ,  5α-Benzylpyrrolidine-2,4-dione ,  Benzoic acid 2β-benzyl-5-oxo-3-pyrroline-3-yl ester ,  N-Boc-L-Isoleucine ,  (5S)-5α-[(S)-sec-Butyl]pyrrolidine-2,4-dione ,  4-Chlorobenzoic acid (2S)-2β-[(S)-1-methylpropyl]-5-oxo-3-pyrroline-3-yl ester ,  (5S)-3-[(Z)-α-Hydroxybenzylidene]-5-benzylpyrrolidine-2,4-dione ,  (5S)-3-[(Z)-1-Hydroxy-2-methylbutylidene]-5α-[(R)-1-(tert-butyldimethylsiloxy)ethyl]pyrrolidine-2,4-dione ,  (5S)-3-[(1Z,2S)-1-Hydroxy-2-methyloctylidene]-5α-[(R)-1-(tert-butyldimethylsiloxy)ethyl]pyrrolidine-2,4-dione ,  Threonine ,  D-Allothreonine ,  N-(Benzyloxycarbonyl)-O-(tert-butyldimethylsilyl)-L-threonine ,  N-(Benzyloxycarbonyl)-O-(tert-butyldimethylsilyl)-D-allothreonine ,  (5S)-5α-[(R)-1-(tert-Butyldimethylsiloxy)ethyl]pyrrolidine-2,4-dione ,  (5R)-5β-[(R)-1-(tert-Butyldimethylsiloxy)ethyl]pyrrolidine-2,4-dione ,  (S)-2-Methyloctanoic acid (2R)-2α-[(R)-1-(tert-butyldimethylsiloxy)ethyl]-5-oxo-3-pyrroline-3-yl ester ,  (5R)-3-[(Z)-1-Hydroxy-2-methyloctylidene]-5β-[(R)-1-(tert-butyldimethylsiloxy)ethyl]pyrrolidine-2,4-dione ,  Penicillenol A₂

Terms in the title (4)： 転位 ,  酸 ,  全合成 ,  応用