title: Total synthesis and biological evaluation of tyroscherin.
abstract: The efficient synthesis and biological evaluation of both the reported and revised structures of tyroscherin have been achieved. Central to our synthesis is a cross metathesis reaction that generated the trans-olefin regioselectively. This synthetic strategy enabled the facile manipulation of tyroscherin stereochemistry, facilitating the generation of all 16 tyroscherin diastereomers and a photoactivatable tyroscherin-based affinity probe for future mode of action studies.
authors.affiliation: Department of Molecular, Cellular, and Developmental Biology, Yale University, New Haven, Connecticut 06511, USA.
authors.forename: Hyun Seop
authors.initials: HS
authors.lastname: Tae
authors.forename: John
authors.initials: J
authors.lastname: Hines
authors.forename: Ashley R
authors.initials: AR
authors.lastname: Schneekloth
authors.forename: Craig M
authors.initials: CM
authors.lastname: Crews
mesh_terms: D045744:Cell Line, Tumor; D004837:Epinephrine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D005233:Fatty Alcohols / Q000138:chemical synthesis* / Q000494:pharmacology; D006801:Humans; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D005233:Fatty Alcohols; C495800:tyroscherin; D004837:Epinephrine