title: Versatile and facile synthesis of diverse semisynthetic tetracycline derivatives via Pd-catalyzed reactions.
abstract: A diverse collection of tetracycline derivatives has been synthesized utilizing Heck, Suzuki, and other palladium-coupling reactions via tetracycline arenediazonium and iodoarene salts. Large numbers of tetracyclines are now possible via these reactions, including numerous upper periphery derivatives of doxycycline, minocycline, sancycline, and methacycline modified at positions C7, C9, and C6-C13 on the tetracycline naphthacene ring. Application of palladium-coupling reactions to the tetracyclines has yielded new tetracycline classes with differing structural attributes, greatly increasing the structural diversity of this family of antibiotics, one of the last of the early antibiotic families to be expanded by organic and medicinal chemistry.
authors.affiliation: Paratek Pharmaceuticals, Inc., 75 Kneeland Street, Boston, Massachusetts 02111, USA. mnelson@paratekpharm.com
authors.forename: Mark L
authors.initials: ML
authors.lastname: Nelson
authors.forename: Mohamed Y
authors.initials: MY
authors.lastname: Ismail
authors.forename: Laura
authors.initials: L
authors.lastname: McIntyre
authors.forename: Beena
authors.initials: B
authors.lastname: Bhatia
authors.forename: Peter
authors.initials: P
authors.lastname: Viski
authors.forename: Paul
authors.initials: P
authors.lastname: Hawkins
authors.forename: Glen
authors.initials: G
authors.lastname: Rennie
authors.forename: David
authors.initials: D
authors.lastname: Andorsky
authors.forename: David
authors.initials: D
authors.lastname: Messersmith
authors.forename: Karen
authors.initials: K
authors.lastname: Stapleton
authors.forename: Jimmy
authors.initials: J
authors.lastname: Dumornay
authors.forename: Paul
authors.initials: P
authors.lastname: Sheahan
authors.forename: Atul K
authors.initials: AK
authors.lastname: Verma
authors.forename: Tadeusz
authors.initials: T
authors.lastname: Warchol
authors.forename: Stuart B
authors.initials: SB
authors.lastname: Levy
mesh_terms: D002384:Catalysis; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D010165:Palladium; D013754:Tetracyclines / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D007202:Indicators and Reagents; D013754:Tetracyclines; D010165:Palladium