Neuramidase inhibitor A-315675 is a pyrrolidine-based compound developed at Abbott Laboratories. This compound exhibits superior activity against certain influenza virus strains when compared to oseltamivir. In this presentation, an efficient asymmetric synthesis of A-315675 is reported. The fully-functionalized pyrrolidine ring is assembled via an exo-selective asymmetric [C+NC+CC] coupling reaction. Subsequent steps involve a Fukuyama thioester reduction and (Z)-selective Wittig olefination.

[C+NC+CC] coupling-enabled synthesis of influenza neuramidase inhibitor A-315675

243rd National Meeting (2012)

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