• Open Access

Total Synthesis of (+)-Linoxepin by Utilizing the Catellani Reaction

Authors


  • We gratefully thank the NSERC, Merck Frosst, and Merck for an Industrial Research Chair. We also thank the University of Toronto for support of our program, Dr. Alan Lough (Chemistry Department, University of Toronto) for single-crystal X-ray structure analysis. H.W. thanks the Austrian Science Fund (FWF): J3250-N19 for an Erwin Schroedinger postdoctoral fellowship and M.S. thanks the DFG for a postdoctoral fellowship. We would like to thank Pierre Thesmar and Patrick Lui for their contributions.

Abstract

original image

Molecular intelligence: The structurally novel lignan (+)-linoxepin is synthesized in an eight-step sequence. The enantioselective synthesis features the palladium-catalyzed Catellani reaction as the key step. In this highly convergent multicomponent reaction, two new carbon–carbon bonds are formed, one of which results from a C[BOND]H bond functionalization.

Ancillary