We have employed an intramolecular pinacol coupling to access the bicyclic core of quinolizidine and indolizidine alkaloids.  In addition to forming the alkaloid B ring, the coupling reaction establishes the C1/C8a relative stereochemistry and provides a handle for the installation of a stereocenter at C2.  The scope and limitations of the reductive coupling as well as efforts to access natural and unnatural hydroxylated alkaloids will be reported.

Quinolizidine and indolizidine alkaloid synthesis via an intramolecular pinacol coupling

243rd National Meeting (2012)

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