408505-25-9Relevant academic research and scientific papers
A highly diastereoselective vinylogous Mannich condensation and 1,4-conjugate addition of (Z)-propenyl cuprate in the synthesis of an influenza neuraminidase inhibitor
Barnes, David M.,Bhagavatula, Lakshmi,DeMattei, John,Gupta, Ashok,Hill, David R.,Manna, Sukumar,McLaughlin, Maureen A.,Nichols, Paul,Premchandran, Ramiya,Rasmussen, Michael W.,Tian, Zhenping,Wittenberger, Steven J.
, p. 3541 - 3551 (2007/10/03)
A practical synthesis of neuraminidase influenza inhibitor, A-322278, has been developed. Asymmetry is introduced into the synthesis by an enzyme mediated ester hydrolysis. A highly diastereoselective vinylogous Mannich condensation reaction of N-Boc-2-te
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.
