471257-47-3Relevant academic research and scientific papers
Process for the preparation of substituted pyrrolidine neuraminidase inhibitors
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, (2008/06/13)
A process for the preparation of neuraminidase inhibitors having structural formula (28) or therapeutically acceptable salts thereof, in which R1 is alkyl, cycloalkyl, cycloalkylalkyl, or arylalkyl; R2 is alkyl, cycloalkyl, cycloalky
Enantioselective synthesis of antiinfluenza compound A-315675
DeGoey, David A.,Chen, Hui-Ju,Flosi, William J.,Grampovnik, David J.,Yeung, Clinton M.,Klein, Larry L.,Kempf, Dale J.
, p. 5445 - 5453 (2007/10/03)
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.
