(-)-Kaitocephalin is a pyrrolidine-based natural product originally isolated from the fungus Eupenicillium shearii. This compound is one of the few naturally occurring glutamate receptor antagonists and displays differential affinity for subtypes of ionotropic glutamic acid receptors (NMDA > AMPA >> KA). In this presentation, our progress towards the efficient asymmetric synthesis of (-)-kaitocephalin will be reported. The fully-functionalized pyrrolidine ring is assembled via an endo-selective asymmetric [C+NC+CC] coupling reaction. Subsequent steps involve a stereoselective aldol reaction to furnish the C3-C4 segment of the molecule, followed by conversion to the target structure.

[C+NC+CC] Coupling-enabled synthesis of the neuroprotective natural product (-)-kaitocephalin

246th National Meeting (2013)

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