title: Synthesis of Microcin SF608 through nucleophilic opening of an oxabicyclo[2.2.1]heptane.
abstract: The total synthesis of Microcin SF608 is reported. Access to the octahydroindole core structure of Microcin SF608 relies on the TMSOTf/NEt(3)-mediated opening of an oxabicyclic ring system. Additional highlights of the synthetic strategy that is reported include a highly regioselective epoxide reduction and photolytic excision of a 3 degrees alcohol.
authors: Laboratorium für Organische Chemie, ETH-Hönggerberg, HCI, H335, CH-8093 Zürich, Switzerland.
authors: Stefan
authors: S
authors: Diethelm
authors: Corinna S
authors: CS
authors: Schindler
authors: Erick M
authors: EM
authors: Carreira
mesh_terms: D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry*; D006536:Heptanes / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D019086:Bridged Bicyclo Compounds, Heterocyclic; D006536:Heptanes; D010455:Peptides; C470082:microcin SF608