Synthesis of Batzelladine F

Significance

Batzelladine F is a metabolite of a red Jamaican sponge. It induces dissociation of two proteins, p56 and CD4, and is of interest for the treatment of autoimmune disease. Extensive synthetic studies by Cohen and Overman (see: J. Am. Chem. Soc. 2006, 128, 2594-2603) established that the structure proposed for Batzelladine F was incorrect. The present paper defines the correct structure and stereochemistry for Batzelladine F and features a tethered Biginelli reaction to construct both of the tricyclic guanidinium rings.