Synthesis of Microcin SF608 through nucleophilic opening of an oxabicyclo[2.2.1]heptane.
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.
Diethelm
Stefan
S
Laboratorium für Organische Chemie, ETH-Hönggerberg, HCI, H335, CH-8093 Zürich, Switzerland.
Schindler
Corinna S
CS
Carreira
Erick M
EM
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
D019086:Bridged Bicyclo Compounds, Heterocyclic; D006536:Heptanes; D010455:Peptides; C470082:microcin SF608