e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

A Diels–Alder-based total synthesis of (−)-kainic acid

A Orellana, SK Pandey, S Carret…

Index: Orellana, Arturo; Pandey, Sushil K.; Carret, Sebastien; Greene, Andrew E.; Poisson, Jean-Francois Journal of Organic Chemistry, 2012 , vol. 77, # 12 p. 5286 - 5296

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Citation Number: 16

Abstract

(−)-Kainic acid (1, Figure 1) is a naturally occurring pyrrolidine with functionalized substituents at C-2, C-3, and C-4 in a trans-cis relationship. Isolated from Digenea simplex in the early 1950s,(1) it was originally used in anthelmintic and insecticide preparations. It is now recognized to be an exceptionally potent glutamate receptor agonist and has become an important tool of biologists for the study of serious neuronal disorders, such as Alzheimer's disease and ...

L-Hydroxyproline Structure

L-Hydroxyproline

~%

(S)-1-TERT-BUTYL 2-METHYL 4-(((TRIFLUOROMETHYL)SULFONYL)OXY)-1H-PYRROLE-1,2(2H,5H)-DICARBOXYLATE Structure

(S)-1-TERT-BUTY...

(2S,4R)-4-hydroxypyrrolidine-2-carbonyl chloride Structure

(2S,4R)-4-hydro...

~%

(S)-1-TERT-BUTYL 2-METHYL 4-(((TRIFLUOROMETHYL)SULFONYL)OXY)-1H-PYRROLE-1,2(2H,5H)-DICARBOXYLATE Structure

(S)-1-TERT-BUTY...

(1S,3aR,7aS)-2-tert-butyl 1-methyl 6-oxo-3,3a,7,7a-tetrahydro-1H-isoindole-1,2(6H)-dicarboxylate Structure

(1S,3aR,7aS)-2-...

~%

Kainic acid Structure

(1S,7aS)-2-(tert-butoxycarbonyl)-6-oxo-2,3,3a,6,7,7a-hexahydro-1H-isoindole-1-carboxylic acid Structure

(1S,7aS)-2-(ter...

~%

Kainic acid Structure

N/A Structure

~%

Kainic acid Structure

(2S,3S,4S)-3-Carboxymethyl-4-(1-methyl-2-oxo-ethyl)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester Structure

(2S,3S,4S)-3-Ca...

~%

Kainic acid Structure

(1S,3aS,7aS)-2-(tert-butoxycarbonyl)-6-oxo-2,3,3a,6,7,7a-hexahydro-1H-isoindole-1,3a-dicarboxylic acid Structure

(1S,3aS,7aS)-2-...

~%

Kainic acid Structure

2-(tert-butyl) 1-methyl (1S,3aR,7aS)-4-methyl-6-((trimethylsilyl)oxy)-1,3,3a,4,7,7a-hexahydro-2H-isoindole-1,2-dicarboxylate Structure

2-(tert-butyl) ...

~%

Kainic acid Structure

(2S,3S,4S)-1-tert-butyl 2-methyl 3-(2-methoxy-2-oxoethyl)-4-((R)-1-oxopropan-2-yl)pyrrolidine-1,2-dicarboxylate Structure

(2S,3S,4S)-1-te...

~%

Kainic acid Structure

(2S,4R)-4-hydroxypyrrolidine-2-carbonyl chloride Structure

(2S,4R)-4-hydro...

~%

Kainic acid Structure

(2S,4R)-METHYL 4-HYDROXYPYRROLIDINE-2-CARBOXYLATE Structure

(2S,4R)-METHYL ...

~%

Kainic acid Structure

Boc-Hyp-OMe Structure

~%

Kainic acid Structure

Boc-4-oxo-Pro-OMe Structure

Boc-4-oxo-Pro-OMe

~%

Kainic acid Structure

L-Hydroxyproline Structure

L-Hydroxyproline

~%

Kainic acid Structure

(S)-1-TERT-BUTYL 2-METHYL 4-(((TRIFLUOROMETHYL)SULFONYL)OXY)-1H-PYRROLE-1,2(2H,5H)-DICARBOXYLATE Structure

(S)-1-TERT-BUTY...

~%

Kainic acid Structure

2-(tert-butyl) 3,7a-dimethyl (3S,3aS,7aS)-7-methoxy-5-((trimethylsilyl)oxy)-3,3a,4,7-tetrahydro-1H-isoindole-2,3,7a-tricarboxylate Structure

2-(tert-butyl) ...

~%

Kainic acid Structure

Syntheses of (+)-cytisine,(-)-kuraramine,(-)-isokuraramine, ...

[Honda, Toshio; Takahashi, Rie; Namiki, Hidenori Journal of Organic Chemistry, 2005 , vol. 70, # 2 p. 499 - 504]

Syntheses of (+)-cytisine,(-)-kuraramine,(-)-isokuraramine, ...

[Honda, Toshio; Takahashi, Rie; Namiki, Hidenori Journal of Organic Chemistry, 2005 , vol. 70, # 2 p. 499 - 504]

Syntheses of (+)-cytisine,(-)-kuraramine,(-)-isokuraramine, ...

[Honda, Toshio; Takahashi, Rie; Namiki, Hidenori Journal of Organic Chemistry, 2005 , vol. 70, # 2 p. 499 - 504]

Syntheses of (+)-cytisine,(-)-kuraramine,(-)-isokuraramine, ...

[Honda, Toshio; Takahashi, Rie; Namiki, Hidenori Journal of Organic Chemistry, 2005 , vol. 70, # 2 p. 499 - 504]