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

Enantioselective synthesis of (-)-kainic acid

…, T Sugihara, S Satoh, K Ogasawara

Index: Takano; Sugihara; Satoh; Ogasawara Journal of the American Chemical Society, 1988 , vol. 110, # 19 p. 6467 - 6471

Full Text: HTML

Citation Number: 78

Abstract

Abstract: Novel diastereoselectivity in the intramolecular Diels-Alder reaction of the heterodiene 18 has been observed. The structure of the cycloadduct was determined to be 20, possessing cis-5/6 ring juncture by converting it into (-)-kainic acid (1) and kainic acid lactone (25).

(R)-benzyl (1-(benzyloxy)-3-oxopropan-2-yl)(3-methylbut-2-en-1-yl)carbamate Structure

(R)-benzyl (1-(...

~%

(2S,3S,4S)-3-(2-acetoxyethyl)-1-(benzyloxycarbonyl)-2-[[(tert-butyldimethylsilyl)-oxy]methyl]-4-isopropenylpyrrolidine Structure

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

(2S,3S,4R)-[1-(benzyloxycarbonyl)-2-(hydroxymethyl)-4-(1-hydroxy-1-methylethyl)]-3-pyrrolidineacetic acid lactone Structure

(2S,3S,4R)-[1-(...

~%

(2S,3S,4S)-3-(2-acetoxyethyl)-1-(benzyloxycarbonyl)-2-[[(tert-butyldimethylsilyl)-oxy]methyl]-4-isopropenylpyrrolidine Structure

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

1-(benzyloxycarbonyl)kainic acid dimethyl ester Structure

1-(benzyloxycar...

~76%

(2S,3S,4S)-1-(benzyloxycarbonyl)-3-(2-hydroxyethyl)-2-(hydroxymethyl)-4-isopropenylpyrrolidine Structure

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

(R)-benzyl (1-(benzyloxy)-3-oxopropan-2-yl)(3-methylbut-2-en-1-yl)carbamate Structure

(R)-benzyl (1-(...

~%

(2S,3S,4S)-1-(benzyloxycarbonyl)-3-(2-hydroxyethyl)-2-(hydroxymethyl)-4-isopropenylpyrrolidine Structure

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

(2S,3S,4S)-benzyl 2-(((tert-butyldimethylsilyl)oxy)methyl)-3-(2-hydroxyethyl)-4-(prop-1-en-2-yl)pyrrolidine-1-carboxylate Structure

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

~%

(2S,3S,4S)-1-(benzyloxycarbonyl)-3-(2-hydroxyethyl)-2-(hydroxymethyl)-4-isopropenylpyrrolidine Structure

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

(2S,3S,4R)-[1-(benzyloxycarbonyl)-2-(hydroxymethyl)-4-(1-hydroxy-1-methylethyl)]-3-pyrrolidineacetic acid lactone Structure

(2S,3S,4R)-[1-(...

~%

(2S,3S,4S)-1-(benzyloxycarbonyl)-3-(2-hydroxyethyl)-2-(hydroxymethyl)-4-isopropenylpyrrolidine Structure

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

(2S,3S,4R)-[1-(benzyloxycarbonyl)-2-[[(tert-butyldimethylsilyl)-oxy]methyl]-4-(1-hydroxy-1-methylethyl)]-3-pyrrolidineacetic acid lactone Structure

(2S,3S,4R)-[1-(...

~96%

(2S,3S,4R)-1-(benzyloxycarbonyl)-2-[[(tert-butyldimethylsilyl)-oxy]methyl]-3-(2-hydroxyethyl)-4-(1-hydroxy-1-methylethyl)pyrrolidine Structure

(2S,3S,4R)-1-(b...

(R)-benzyl (1-(benzyloxy)-3-oxopropan-2-yl)(3-methylbut-2-en-1-yl)carbamate Structure

(R)-benzyl (1-(...

~%

(2S,3S,4R)-1-(benzyloxycarbonyl)-2-[[(tert-butyldimethylsilyl)-oxy]methyl]-3-(2-hydroxyethyl)-4-(1-hydroxy-1-methylethyl)pyrrolidine Structure

(2S,3S,4R)-1-(b...

(2S,3S,4R)-[1-(benzyloxycarbonyl)-2-(hydroxymethyl)-4-(1-hydroxy-1-methylethyl)]-3-pyrrolidineacetic acid lactone Structure

(2S,3S,4R)-[1-(...

~%

(2S,3S,4R)-1-(benzyloxycarbonyl)-2-[[(tert-butyldimethylsilyl)-oxy]methyl]-3-(2-hydroxyethyl)-4-(1-hydroxy-1-methylethyl)pyrrolidine Structure

(2S,3S,4R)-1-(b...

(R)-benzyl (1-(benzyloxy)-3-oxopropan-2-yl)(3-methylbut-2-en-1-yl)carbamate Structure

(R)-benzyl (1-(...

~%

(2S,3S,4R)-[1-(benzyloxycarbonyl)-2-[[(tert-butyldimethylsilyl)-oxy]methyl]-4-(1-hydroxy-1-methylethyl)]-3-pyrrolidineacetic acid lactone Structure

(2S,3S,4R)-[1-(...

(R)-benzyl (1-(benzyloxy)-3-oxopropan-2-yl)(3-methylbut-2-en-1-yl)carbamate Structure

(R)-benzyl (1-(...

~%

(2S,3S,4R)-[1-(benzyloxycarbonyl)-2-(hydroxymethyl)-4-(1-hydroxy-1-methylethyl)]-3-pyrrolidineacetic acid lactone Structure

(2S,3S,4R)-[1-(...

(R)-benzyl (1-(benzyloxy)-3-oxopropan-2-yl)(3-methylbut-2-en-1-yl)carbamate Structure

(R)-benzyl (1-(...

~%

1-(benzyloxycarbonyl)kainic acid dimethyl ester Structure

1-(benzyloxycar...

(2S,3S,4S)-1-(benzyloxycarbonyl)-3-(2-hydroxyethyl)-2-(hydroxymethyl)-4-isopropenylpyrrolidine Structure

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

~%

1-(benzyloxycarbonyl)kainic acid dimethyl ester Structure

1-(benzyloxycar...

(2S,3S,4R)-[1-(benzyloxycarbonyl)-2-(hydroxymethyl)-4-(1-hydroxy-1-methylethyl)]-3-pyrrolidineacetic acid lactone Structure

(2S,3S,4R)-[1-(...

~%

1-(benzyloxycarbonyl)kainic acid dimethyl ester Structure

1-(benzyloxycar...

(2S,3S,4S)-benzyl 2-(((tert-butyldimethylsilyl)oxy)methyl)-3-(2-hydroxyethyl)-4-(prop-1-en-2-yl)pyrrolidine-1-carboxylate Structure

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

~%

1-(benzyloxycarbonyl)kainic acid dimethyl ester Structure

1-(benzyloxycar...

(R)-benzyl (1-(benzyloxy)-3-oxopropan-2-yl)(3-methylbut-2-en-1-yl)carbamate Structure

(R)-benzyl (1-(...

~%

(2S,3S,4S)-benzyl 2-(((tert-butyldimethylsilyl)oxy)methyl)-3-(2-hydroxyethyl)-4-(prop-1-en-2-yl)pyrrolidine-1-carboxylate Structure

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

(2S,3S,4R)-[1-(benzyloxycarbonyl)-2-(hydroxymethyl)-4-(1-hydroxy-1-methylethyl)]-3-pyrrolidineacetic acid lactone Structure

(2S,3S,4R)-[1-(...

~%

(2S,3S,4S)-benzyl 2-(((tert-butyldimethylsilyl)oxy)methyl)-3-(2-hydroxyethyl)-4-(prop-1-en-2-yl)pyrrolidine-1-carboxylate Structure

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

(2S,3S,4R)-[1-(benzyloxycarbonyl)-2-[[(tert-butyldimethylsilyl)-oxy]methyl]-4-(1-hydroxy-1-methylethyl)]-3-pyrrolidineacetic acid lactone Structure

(2S,3S,4R)-[1-(...

~%

(2S,3S,4S)-benzyl 2-(((tert-butyldimethylsilyl)oxy)methyl)-3-(2-hydroxyethyl)-4-(prop-1-en-2-yl)pyrrolidine-1-carboxylate Structure

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