Total synthesis of the ethyl ester of the major urinary metabolite of prostaglandin E(2).
The preparation of the ethyl ester of the major urinary metabolite of prostaglandin E(2) 3 is described. The key step is the kinetic opening of the TBS-protected bicyclic ketone 7 with thiophenol.
Taber
Douglass F
DF
Department of Chemistry & Biochemistry, University of Delaware, Newark, Delaware 19716, USA. taberd@udel.edu
Teng
Dawei
D
D002625:Chemistry, Organic / Q000379:methods; D015232:Dinoprostone / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry / Q000652:urine; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry; D004980:Ethane / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism
D004952:Esters; D015232:Dinoprostone; D004980:Ethane