title: Synthesis of new 14-membered macrolide antibiotics via a novel ring contraction metathesis.
abstract: [reaction: see text] A novel ring opening ring closing metathesis (ROM-RCM) was demonstrated for cyclic conjugated dienes, effecting the excision of a C(2)H(2) unit and a net ring contraction. Applying the ring contraction metathesis, new 14-membered ring macrolide antibiotics were synthesized in a single step from existing 16-membered ring macrolides. This new class of macrolide antibiotics will provide access to new therapeutics for the treatment of macrolide-resistant bacterial infections.
authors.affiliation: Enanta Pharmaceuticals, 500 Arsenal Street, Watertown, Massachusetts 02472, USA. tsvetelina.lazarova@sprlus.com
authors.forename: Tsvetelina I
authors.initials: TI
authors.lastname: Lazarova
authors.forename: Sophie M
authors.initials: SM
authors.lastname: Binet
authors.forename: Nha H
authors.initials: NH
authors.lastname: Vo
authors.forename: Jason S
authors.initials: JS
authors.lastname: Chen
authors.forename: Ly T
authors.initials: LT
authors.lastname: Phan
authors.forename: Yat Sun
authors.initials: YS
authors.lastname: Or
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D004351:Drug Resistance; D004917:Erythromycin / Q000737:chemistry; D015570:Josamycin / Q000737:chemistry; D013296:Streptococcus pneumoniae / Q000187:drug effects; D013297:Streptococcus pyogenes / Q000187:drug effects; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D004917:Erythromycin; D015570:Josamycin