Sequential C–H Functionalization Reactions for the Enantioselective Synthesis of Highly Functionalized 2,3-Dihydrobenzofurans

Hengbin Wang, Gang Li, Keary M. Engle, Jin-Quan Yu and Huw M. L. Davies

J. Am. Chem. Soc.,
2013, 6774-6777; 10.1021/ja401731d


This collaborative project brought together the groups of Prof. Huw Davies at Emory University, Atlanta Georgia and Prof. Jin-Quan Yu from The Scripps Research Institute at La Jolla California.

The project uses a series of three sequential C-H Functionalizations to rapidly assemble, in a stereocontrolled fashion, the structural core of the Lithospermic family of natural products. The sequence employs a C-H Functionalization previously established by the Davies group, a C-H Functionalization previously developed by the Yu group and an entirely novel C-H Functionalization developed during these studies. Not only does this C-H Functionalization-based strategy provide a method for rapid contruction of this complex core structure, but the methdology is highly modular, provide ready access to a braod library of lithospermic analogues.

The researchers involved in this project futher benefited from being involved in the CCHF by carrying out a student exchange. Hengbin Wang, (pictured here at TSRI with Keary Engle), from the Davies Group, travelled to TSRI and worked in the Yu lab for four weeks, sharing ideas and methods with his collaborative co-workers. This exchange was not only an excellent learning experience, but also accelerated the completion of this project.

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