When the target of a chemical synthesis endeavor contains one or more stereogenic quaternary carbons, how to assemble these quaternary stereocenters becomes a central component of synthesis planning and execution. Many factors contribute to this challenge: steric hindrance, the need generally to forge such carbon centers by C�C bond formation, and the inability in most situations to invert quaternary stereocenters. That the chemical synthesis of such carbons is particularly challenging can be seen in the structures of existing pharmaceutical agents. Of the 150 top-selling brand-name drugs in 2008, the only ones that contain stereogenic quaternary carbons are steroid or opioid derivatives, which undoubtedly are prepared by semisynthesis.This lecture will consider how the challenge of constructing stereogenic quaternary carbons was tackled in several recent and ongoing total synthesis endeavors in our laboratories.

Construction of stereogenic quaternary carbons in polycyclic natural products

243rd National Meeting (2012)

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