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

Concise stereoselective synthesis of (2 S, 4 R)-4-hydroxyproline from (S)-O-benzylglycidol a novel cyclization

S Takano, Y Iwabuchi, K Ogasawara

Index: Takano, Seiichi; Iwabuchi, Yoshiharu; Ogasawara, Kunio Journal of the Chemical Society, Chemical Communications, 1988 , # 23 p. 1527 - 1528

Full Text: HTML

Citation Number: 17

Abstract

Concise Stereoselective Synthesis of (2S,4R)-4-Hydroxyproline from (S)-0-Benzylglycidol by a Novel Cyclization ... Seiichi Takano," Yoshiharu Iwabuchi, and Kunio Ogasawara Pharmaceutical Institute, Tohoku University, Aoba yama, Sendai 980, Japan ... An efficient stereoselective route to (2S,4R)-4-hydroxyproIine from (S)-0-benzylglycidol has been established via a novel iodine-mediated cyclization of the N-benzoyl-y,G-unsaturated amide.

(2R)-1-benzyloxy-2-hydroxy-pent-4-yne Structure

(2R)-1-benzylox...

~%

(2S,4R)-tert-butyl 2-((benzyloxy)methyl)-4-hydroxypyrrolidine-1-carboxylate Structure

(2S,4R)-tert-bu...

(2S,4R)-tert-butyl 4-(benzoyloxy)-2-((benzyloxy)methyl)pyrrolidine-1-carboxylate Structure

(2S,4R)-tert-bu...

~%

(2S,4R)-tert-butyl 2-((benzyloxy)methyl)-4-hydroxypyrrolidine-1-carboxylate Structure

(2S,4R)-tert-bu...

(S)-1-(benzyloxy)pent-4-en-2-amine Structure

(S)-1-(benzylox...

~%

(2S,4R)-tert-butyl 2-((benzyloxy)methyl)-4-hydroxypyrrolidine-1-carboxylate Structure

(2S,4R)-tert-bu...

(S)-N-(1-(benzyloxy)pent-4-en-2-yl)benzamide Structure

(S)-N-(1-(benzy...

~%

(2S,4R)-tert-butyl 2-((benzyloxy)methyl)-4-hydroxypyrrolidine-1-carboxylate Structure

(2S,4R)-tert-bu...

O-benzyl-(2S,4R)-4-benzoyloxyprolinol Structure

O-benzyl-(2S,4R...

~%

(2S,4R)-tert-butyl 2-((benzyloxy)methyl)-4-hydroxypyrrolidine-1-carboxylate Structure

(2S,4R)-tert-bu...

(S)-2-(1-(benzyloxy)pent-4-en-2-yl)isoindoline-1,3-dione Structure

(S)-2-(1-(benzy...

~%

(2S,4R)-tert-butyl 2-((benzyloxy)methyl)-4-hydroxypyrrolidine-1-carboxylate Structure

(2S,4R)-tert-bu...

(2R)-1-benzyloxy-2-hydroxy-pent-4-yne Structure

(2R)-1-benzylox...

~%

(2S,4R)-tert-butyl 4-(benzoyloxy)-2-((benzyloxy)methyl)pyrrolidine-1-carboxylate Structure

(2S,4R)-tert-bu...

(S)-1-(benzyloxy)pent-4-en-2-amine Structure

(S)-1-(benzylox...

~%

(2S,4R)-tert-butyl 4-(benzoyloxy)-2-((benzyloxy)methyl)pyrrolidine-1-carboxylate Structure

(2S,4R)-tert-bu...

(S)-N-(1-(benzyloxy)pent-4-en-2-yl)benzamide Structure

(S)-N-(1-(benzy...

~%

(2S,4R)-tert-butyl 4-(benzoyloxy)-2-((benzyloxy)methyl)pyrrolidine-1-carboxylate Structure

(2S,4R)-tert-bu...

(S)-2-(1-(benzyloxy)pent-4-en-2-yl)isoindoline-1,3-dione Structure

(S)-2-(1-(benzy...

~%

(2S,4R)-tert-butyl 4-(benzoyloxy)-2-((benzyloxy)methyl)pyrrolidine-1-carboxylate Structure

(2S,4R)-tert-bu...

(S)-N-(1-(benzyloxy)pent-4-en-2-yl)benzamide Structure

(S)-N-(1-(benzy...

~79%

O-benzyl-(2S,4R)-4-benzoyloxyprolinol Structure

O-benzyl-(2S,4R...

(2R)-1-benzyloxy-2-hydroxy-pent-4-yne Structure

(2R)-1-benzylox...

~%

O-benzyl-(2S,4R)-4-benzoyloxyprolinol Structure

O-benzyl-(2S,4R...

(S)-1-(benzyloxy)pent-4-en-2-amine Structure

(S)-1-(benzylox...

~%

O-benzyl-(2S,4R)-4-benzoyloxyprolinol Structure

O-benzyl-(2S,4R...

(S)-2-(1-(benzyloxy)pent-4-en-2-yl)isoindoline-1,3-dione Structure

(S)-2-(1-(benzy...

~%

O-benzyl-(2S,4R)-4-benzoyloxyprolinol Structure

O-benzyl-(2S,4R...

(2R)-1-benzyloxy-2-hydroxy-pent-4-yne Structure

(2R)-1-benzylox...

~%

(S)-N-(1-(benzyloxy)pent-4-en-2-yl)benzamide Structure

(S)-N-(1-(benzy...

(S)-2-(1-(benzyloxy)pent-4-en-2-yl)isoindoline-1,3-dione Structure

(S)-2-(1-(benzy...

~%

(S)-N-(1-(benzyloxy)pent-4-en-2-yl)benzamide Structure

(S)-N-(1-(benzy...

Benzoyl chloride Structure

Benzoyl chloride

(S)-1-(benzyloxy)pent-4-en-2-amine Structure

(S)-1-(benzylox...

~%

(S)-N-(1-(benzyloxy)pent-4-en-2-yl)benzamide Structure

(S)-N-(1-(benzy...

(2R)-1-benzyloxy-2-hydroxy-pent-4-yne Structure

(2R)-1-benzylox...

~%

(S)-1-(benzyloxy)pent-4-en-2-amine Structure

(S)-1-(benzylox...

(S)-2-(1-(benzyloxy)pent-4-en-2-yl)isoindoline-1,3-dione Structure

(S)-2-(1-(benzy...

~%

(S)-1-(benzyloxy)pent-4-en-2-amine Structure

(S)-1-(benzylox...

(2R)-1-benzyloxy-2-hydroxy-pent-4-yne Structure

(2R)-1-benzylox...

~%

(S)-2-(1-(benzyloxy)pent-4-en-2-yl)isoindoline-1,3-dione Structure

(S)-2-(1-(benzy...

(2R)-1-benzyloxy-2-hydroxy-pent-4-yne Structure

(2R)-1-benzylox...

~%

(2S,4R)-4-(benzoyloxy)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid Structure

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

(2S,4R)-tert-butyl 4-(benzoyloxy)-2-((benzyloxy)methyl)pyrrolidine-1-carboxylate Structure

(2S,4R)-tert-bu...

~%

(2S,4R)-4-(benzoyloxy)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid Structure

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

(S)-1-(benzyloxy)pent-4-en-2-amine Structure

(S)-1-(benzylox...

~%

(2S,4R)-4-(benzoyloxy)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid Structure

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

(S)-N-(1-(benzyloxy)pent-4-en-2-yl)benzamide Structure

(S)-N-(1-(benzy...

~%

(2S,4R)-4-(benzoyloxy)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid Structure

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

O-benzyl-(2S,4R)-4-benzoyloxyprolinol Structure

O-benzyl-(2S,4R...

~%

(2S,4R)-4-(benzoyloxy)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid Structure

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

(S)-2-(1-(benzyloxy)pent-4-en-2-yl)isoindoline-1,3-dione Structure

(S)-2-(1-(benzy...

~%

(2S,4R)-4-(benzoyloxy)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid Structure

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