Total synthesis and biological evaluation of tyroscherin.
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.
Tae
Hyun Seop
HS
Department of Molecular, Cellular, and Developmental Biology, Yale University, New Haven, Connecticut 06511, USA.
Hines
John
J
Schneekloth
Ashley R
AR
Crews
Craig M
CM
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
D005233:Fatty Alcohols; C495800:tyroscherin; D004837:Epinephrine