| Literature DB >> 27794616 |
Xudong Wei1, Bo Qu1, Xingzhong Zeng1, Jolaine Savoie1, Keith R Fandrick1, Jean-Nicolas Desrosiers1, Sergei Tcyrulnikov2, Maurice A Marsini1, Frederic G Buono1, Zhibin Li1, Bing-Shiou Yang1, Wenjun Tang1, Nizar Haddad1, Osvaldo Gutierrez2, Jun Wang1, Heewon Lee1, Shengli Ma1, Scot Campbell1, Jon C Lorenz1, Matthias Eckhardt3, Frank Himmelsbach3, Stefan Peters3, Nitinchandra D Patel1, Zhulin Tan1, Nathan K Yee1, Jinhua J Song1, Frank Roschangar1, Marisa C Kozlowski2, Chris H Senanayake1.
Abstract
A concise asymmetric synthesis of an 11β-HSD-1 inhibitor has been achieved using inexpensive starting materials with excellent step-economy at low catalyst loadings. The catalytic enantioselective total synthesis of 1 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]2.Entities:
Mesh：
Substances：
Year: 2016 PMID： 27794616 PMCID： PMC5243942 DOI： 10.1021/jacs.6b09764
Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419