Abstract

An asymmetric synthetic approach to the octahydrofuro[3,4-b]pyridine framework of marine natural product zamamiphidin A has been described. The key steps include an asymmetric Michael addition of (R)-N-tert-butanesulfinyl imidate with enamidomalonate to install the C10 stereocenter, an intramolecular alkoxide exchange/Michael addition/hydrogenation sequence to construct the bicyclic ring system.

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