Art

J-GLOBAL ID：202002247291777502   Reference number：20A1237852

Chiral Lewis Acid-template Diels-Alder Reaction and the Application of Natural Product Synthesis

キラルLewis酸テンプレートを用いる不斉Diels-Alder反応と天然物合成への応用

Author (1)： ISHIHARA JUN (長崎大学生命医科学域)
Material： 有機合成化学協会誌  (Journal of Synthetic Organic Chemistry, Japan)
Volume： 78  Issue： 3  Page： 204-212(J-STAGE)  Publication year： 2020 
JST Material Number： F0383A  ISSN： 0037-9980  CODEN： YGKKAE  Document type： Article
Article type： 原著論文  Country of issue： Japan (JPN)  Language： JAPANESE (JA)

Thesaurus term： asymmetric synthesis ,  catalytic reaction ,  metal catalyst ,  Lewis acid catalyst ,  *Diels-Alder reaction ,  tether ,  intramolecular interaction ,  diene ,  enol ,  aldehyde ,  *lactone ,  *polynuclear aromatic compound ,  enantiomer ,  Lewis acid ,  bimetallic catalyst ,  hetero Diels-Alder reaction ,  intramolecular Diels-Alder reaction ,  intramolecular reaction ,  *Pyrans ,  *Benzofurans ,  unsaturated fatty acid ,  vinyl compound ,  carboxylate (ester)
Semi thesaurus term： *Pyrans ,  *Benzofurans

Author keywords (7)： Lewis acid ,  template ,  Diels-Alder reaction ,  bimetallic catalyst ,  bicyclic lactone ,  natural product synthesis ,  spirolide

JST classification (3)： Catalytic reactions in general  (CB06080F) ,  Cyclohexanes  (CF04050W) ,  Pyranes  (CF07092R)

Substance index (23)： (R)-1-(Phenylthio)-3,5-heptadiene-2-ol ,  (2S)-2β-[4-(Trimethylsilyl)-3-butynyl]-3β,6β-dimethyl-4-(triethylsiloxy)-3,6-dihydro-2H-pyran ,  (2S)-2β-Methyl-6β-(phenylethynyl)tetrahydro-4H-pyran-4-one ,  3β,6β-Dimethyl-4-(tert-butyldimethylsilyloxy)-3,6-dihydro-2H-pyran-2α-carboxylic acid ethyl ester ,  (3aR)-4,5-Dimethyl-3aα,6,7,7aα-tetrahydroisobenzofuran-1(3H)-one ,  (3aR)-4-Methyl-3aα,6,7,7aα-tetrahydroisobenzofuran-1(3H)-one ,  (3aR,7aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-methyl-3a,6,7,7a-tetrahydro-3H-2-benzofuran-1-one ,  3aα,6,7,7aα-Tetrahydroisobenzofuran-1(3H)-one ,  (3aS)-5-[2-(Benzyloxy)ethyl]-3aα,6,7,7aα-tetrahydroisobenzofuran-1(3H)-one ,  (3aS)-5-Methyl-3aα,6,7,7aα-tetrahydroisobenzofuran-1(3H)-one ,  5α-Methyl-3-oxo-1,3,3aβ,4,5,7aβ-hexahydroisobenzofuran ,  3β-(Phenylthiomethyl)-6α-methyl-1,3,3aβ,6,7,7aβ-hexahydroisobenzofuran-1-one ,  2,4-Hexadien-1-ol ,  3-メチル-4-[(4R)-2,2-ジメチル-1,3-ジオキソラン-4-イル]-2,4-ペンタジエン-1-オール ,  4-Methyl-2,4-pentadiene-1-ol ,  5,5′-Bi(tetralin-6-ol) ,  Acrylic acid methyl ,  Abyssomicin C ,  Spirolide A ,  Spirolide B ,  Spirolide C ,  Spirolide D ,  Hirsutellone B

Reference (74)：

• 1) (a) W. R. Roush, “Comprehensive Organic Synthesis”, Vol. 5, eds. by B. M. Trost, I. Fleming, L. A. Paquette, Pergamon, Oxford, 1991, p 513
• (b) D. Tanner, E. Ascic, “Comprehensive Organic Synthesis”, Vol. 5, 2 nd edition, eds. by G. A. Molander, P. Knochel, Elsevier, Oxford, 2014, p 466
• (c) D. Craig, Chem. Soc. Rev., 16, 187 (1987)
• (d) A. G. Fallis, Can. J. Chem., 62, 183 (1984)
• 2) K. Tamao, K. Kobayashi, Y. Ito, J. Am. Chem. Soc., 111, 6478 (1989)

Terms in the title (5)： キラル ,  Lewis酸 ,  テンプレート ,  天然物合成 ,  応用