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Prostaglandin E2 is produced in response to inflammation, often associated with human disease. As prostaglandins are rapidly metabolized, quantification of end urinary metabolites depend on chemical synthesis of isotopically labeled standards to support metabolite quantification. A concise synthesis of tetranor-PGE1 is described including a late stage incorporation of an isotopically labeled side-chain.Reductive late-stage functionalization of gibberellic acid is reported using three fluoroarylborane Lewis acids; (B(C6F5)3, B(3,5-C6H3(C
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