An Efficient, Optimized Synthesis of Fentanyl and Related Analogs.PDF - An Efficient,Optimized Synthesis of Fentanyl and Related Analogs Carlos A

An Efficient, Optimized Synthesis of Fentanyl and Related Analogs.PDF

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An Efficient,Optimized Synthesis of FentanylandRelated AnalogsCarlos A. Valdez1,2, Roald N. Leif1,2, Brian P. Mayer1,2*1 Physicaland Life Sciences Directorate,Lawrence Livermore NationalLaboratory,Livermore,California,United States of America,2 Forensic Science Center,LawrenceLivermore NationalLaboratory,Livermore,California,United States of AmericaAbstractThe alternate and optimized syntheses of the parent opioid fentanyland its analogs are described.The routes presentedexhibit high-yielding transformations leading to these powerfulanalgesics after optimization studies were carried out foreach synthetic step.The generalthree-step strategy produced a panelof four fentanyls in excellent yields (73–78%) alongwith their more commonly encountered hydrochloride and citric acid salts. The following strategy offers the opportunitythe gram-scale,efficient production of this interesting class of opioid alkaloids.Citation: Valdez CA,Leif RN,Mayer BP (2014) An Efficient,Optimized Synthesis of Fentanyland Related Analogs.PLoS ONE 9(9):e108250.doi:10.1371/journal.pone.0108250Editor: Martina Lahmann,Bangor University,United KingdomReceived July 29,2014;Accepted August 26,2014;Published September 18,2014Copyright:ß2014 Valdez etal.This is an open-access article distributed underthe terms ofthe Creative Commons Attribution License,which permitsunrestricted use,distribution,and reproduction in any medium,provided the originalauthor and source are credited.Data Availability: The authors confirm that all data underlying the findings are fully available without restriction.All relevant data are within the paper and itsSupporting Information files.Funding: The authors (CAV, BPM, and RNL) received funding from Lawrence Livermore National Laboratory ( under the Laboratory Directed ResearchDevelopment(LDRD)program,projectnumber14-ERD-048.The funders had no role in study design,data collection and analysis,decision to publish,orpreparation of the manuscript.Competing Interests: The authors have declared that no competing interests exist.* Email:[email protected]IntroductionVery few synthetic drugs generate an immediate and powerfulimpactin the biomedicalfield shortly after their inception.Thishasbeen the case particularly within the areasof pre-surgical,surgical,and post-surgicalanesthesiology where the need for fastacting,effective pain relieversis a key elementin the overallpatient care practice.Morphine (1)and Tramadol(2)(Fig.1)aretwo opioid-based compounds that are widely recognized for beingthe gold standard prescriptionsfor patientswith moderate tosevere pain after surgery or with certain disease states (e.g. cancer)[1–6]. Due to their potency, these therapeutics, however, are alsowellknown for their ability to foster chemicaldependenciesinpatients and other users [7].
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