The talk will focus on successful efforts to develop a synthesis amenable to scale-up for toxicological and clinical supplies for a tetracyclic GPR40 agonist containing 4 stereocenters.  Highlights of the work include efficient establishment of the stereochemical configuration on the C ring, formation of the A ring via a [3+2] with regio- and stereochemistry control, a challenging cross-coupling to merge the AB and CD ring fragments, and finally a optimized process to purge impurities in the final 2 steps solely via pH controlled solubility and crystallization thus obviating the use of column chromatography.

Scaleable synthesis of a GPR40 agonist

248th National Meeting (2014)

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