A highly diastereoselective vinylogous Mannich condensation and 1, 4-conjugate addition of (Z)-propenyl cuprate in the synthesis of an influenza neuraminidase …

DM Barnes, L Bhagavatula, J DeMattei, A Gupta…

Index: 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. Tetrahedron Asymmetry, 2003 , vol. 14, # 22 p. 3541 - 3551

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Citation Number: 31

Abstract

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-tert- butyldimethylsilyloxypyrrole (TBSOP) and an N-(triphenylmethylsulfenyl) imine proceeds under thermodynamic control to assemble the framework. A significant temperature ...