title: A Divergent Route to Eravacycline.
abstract: A convergent route to eravacycline (1) has been developed by employing Michael-Dieckmann cyclization between enone 3 and a fully built and protected left-hand piece (LHP, 2). After construction of the core eravacycline structure, a deprotection reaction was developed, allowing for the isoxazole ring opening and global deprotection to be achieved in one pot. The LHP is synthesized from readily available 4-fluoro-3-methylphenol in six steps featuring a palladium-catalyzed phenyl carboxylation in the last step.
authors.affiliation: Tetraphase Pharmaceuticals, Inc. , 480 Arsenal Way, Suite 110, Watertown, Massachusetts 02472, United States.
authors.forename: Wu-Yan
authors.identifier: 0000-0002-4858-4784
authors.initials: WY
authors.lastname: Zhang
authors.affiliation: Tetraphase Pharmaceuticals, Inc. , 480 Arsenal Way, Suite 110, Watertown, Massachusetts 02472, United States.
authors.forename: Qinglin
authors.initials: Q
authors.lastname: Che
authors.affiliation: Tetraphase Pharmaceuticals, Inc. , 480 Arsenal Way, Suite 110, Watertown, Massachusetts 02472, United States.
authors.forename: Scott
authors.initials: S
authors.lastname: Crawford
authors.affiliation: Tetraphase Pharmaceuticals, Inc. , 480 Arsenal Way, Suite 110, Watertown, Massachusetts 02472, United States.
authors.forename: Magnus
authors.initials: M
authors.lastname: Ronn
authors.affiliation: Tetraphase Pharmaceuticals, Inc. , 480 Arsenal Way, Suite 110, Watertown, Massachusetts 02472, United States.
authors.forename: Nicholas
authors.initials: N
authors.lastname: Dunwoody
mesh_terms: D003408:Cresols / Q000737:chemistry; D003500:Cyclization; D015394:Molecular Structure; D013754:Tetracyclines / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D003408:Cresols; D013754:Tetracyclines; C571179:eravacycline; C077977:cresol