335679-69-1

Upstream product

• 1567-14-2 methyl (2E)-2-methyl-2-pentenoate 
• 408505-25-9 (2R,3S)-5-Methoxy-2-((1R,2S)-2-methoxy-2-methyl-1-tritylsulfanylamino-pentyl)-3-((Z)-propenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 408505-26-0 tert-butyl (2R,3S,5R)-5-cyano-2-{(1R,2S)-2-methoxy-2-methyl-1-[(tritylthio)amino]pentyl}-3-[(1Z)-prop-1-enyl]pyrrolidine-1-carboxylate 
• 335693-75-9 (1S,2S)-(1-formyl-2-methoxy-2-methylpentyl)-carbamic acid tert-butyl ester 
• 433711-92-3 N-{(2S)-methoxy-(1R)-[1-(2,4-dimethoxybenzyl)-5-oxo-(3S)-Z-propenylpyrrolidin-(2R)-yl]-(2S)-methylpentyl}-acetamide 
• 433711-81-0 (5R)-tert-butoxycarbonylamino-(4R)-[hydroxy-(4-methoxybenzyl)-amino]-(6S)-methoxy-(6S)-methylnon-2-ynoic acid ethyl ester 
• 433711-82-1 (5R)-tert-butoxycarbonylamino-(4R)-[hydroxy-(4-methoxybenzyl)-amino]-(6S)-methoxy-(6S)-methylnon-2-ynoic acid tert-butyl ester 
• 433711-89-8 {(2S)-methoxy-(1R)-[1-(2,4-dimethoxy)-benzyl-5-oxo-(3S)-Z-propenylpyrrolidin-(2R)-yl]-(2S)-methylpentyl}-carbamic acid tert-butyl ester 
• 433711-87-6 (5R)-tert-butoxycarbonylamino-(4R)-[hydroxy-(2,4-dimethoxybenzyl)-amino]-(6S)-methoxy-(6S)-methylnon-2-ynoic acid ethyl ester 
• 16958-19-3 (2E)-2-methyl-2-penten-1-ol 
• 335692-78-9 tert-butyl (2R,3S,5R)-5-cyano-2-{(1R,2S)-2-methoxy-2-methyl-1-[(acetylamino)pentyl]}-3-[(1Z)-prop-1-enyl]pyrrolidine-1-carboxylate 
• 335693-23-7 tert-butyl (2R)-2-{(1R,2S)-2-methoxy-2-methyl-1-[(triphenylmethylsulfenyl)amino]pentyl}-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate 
• 335679-41-9 (2R,3S,5R,1'R,2'S)-2-(1-Acetamido-2-methyl-2-methoxy)pentyl-3-(cis-propen-1-yl)-pyrrolidine-5-carboxylic Acid Ethyl Ester 
• 433711-91-2 (4S,5R)-5-((1R,2S)-1-Amino-2-methoxy-2-methyl-pentyl)-1-(2,4-dimethoxy-benzyl)-4-((Z)-propenyl)-pyrrolidin-2-one 

Relevant academic research and scientific papers

Total synthesis of A-315675 based on the cascade Overman rearrangement

The chiral and stereoselective total synthesis of A-315675 1, an antiinfluenza agent, is described. The vicinal diamino moiety in 1 was stereoselectively constructed by the cascade Overman rearrangement of a vicinal allylic-homoallylic diol derived from d

Enantioselective synthesis of antiinfluenza compound A-315675

Drug discovery efforts at Abbott Laboratories have led to the identification of influenza neuraminidase inhibitor A-315675 (1) as a candidate for development as an antiinfluenza drug. A convergent, stereoselective synthesis of this highly functionalized pyrrolidine is reported that utilizes pyrrolinone 2 as the key intermediate. The C5, C6 stereochemistry was established through a diastereoselective condensation of chiral imine compound 3 with silyloxypyrrole 4 to give pyrrolinone 2. The stereochemical outcome of this reaction depended critically on the choice of the imine functional group (FG), with tritylsulfenyl and (R)-toluenesulfinyl providing the desired products in good yields as crystalline intermediates. Conversion of pyrrolinone 2 into 1 was accomplished in seven subsequent steps, including Michael addition of cis-1-propenylcuprate at C4 and introduction of a cyano group as a carboxylic acid equivalent at C2.

Total synthesis of A-315675: A potent inhibitor of influenza neuraminidase

A concise, stereocontrolled, and practical synthesis of a neuraminidase inhibitor consisting of a highly functionalized D-proline scaffold is described. Key features involve a stereocontrolled addition of a propiolate ester to a chiral nonracemic nitrone

Inhibitors of neuraminidases

Disclosed are compounds of the formula: which are useful for inhibiting neuraminidases from disease-causing microorganisms, especially, influenza neuraminidase. Also disclosed are compositions and methods for preventing and treating diseases caused by mic