A concise asymmetric synthesis of an 11β-HSD-1 inhibitor has been achieved starting from inexpensive raw materials with excellent step-economy at low catalyst loadings. The catalytic enantioselective synthesis was accomplished in 7 steps and 38% overall yield aided by the development of an innovative, sequential strategy involving Pd-catalyzed pyridinium C-H arylation and Ir-catalyzed asymmetric hydrogenation of the resulting fused tricyclic indenopyridinium salt highlighted by the use of a unique P,N-ligand (MeO-BoQPhos) with 1000 ppm of [Ir(COD)Cl]<sub>2</sub>.

Development of an ideal asymmetric synthesis for BI’s 11β-HSD 1 inhibitor

255th National Meeting (2018)

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