Synthesis of diverse tetracycline derivatives via Pd-catalyzed reactions: Creation of a large collection of novel 3rd generation tetracyclines

ORGN 454

Mark L. Nelson, mnelson@paratekpharm.com, Laura Honeyman, Mohamed Ismail, Beena Bhatia, Atul K. Verma, Tadeusz Warchol, Todd Bowser, Joel Berniac, Rachid Mechiche, Paul Abato, and Haregewein Assefa. Paratek Pharmaceuticals, Inc, 75 Kneeland St, Boston, MA 02111
A diverse collection of tetracycline derivatives has been synthesized by palladium-coupling reactions via tetracycline arenediazonium and iodoarene intermediates of the second generation tetracyclines, namely, minocycline, doxycycline, sancycline, and methacycline. Derivatives are now possible at positions C7, C8, C9 and C13 of the tetracycline naphthacene ring system, yielding new classes with different structural attributes, dramatically increasing the structural diversity of the tetracycline family of antibiotics. Preliminary biological uses are also presented in bacteriology and parasitology.
 

Metal-Mediated Reactions and Syntheses
8:00 AM-12:00 PM, Wednesday, 29 March 2006 Georgia World Congress Center -- C302, Oral

Division of Organic Chemistry

The 231st ACS National Meeting, Atlanta, GA, March 26-30, 2006