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Synthesis of [¹⁸F]-?-fluoro-?,?,-unsaturated esters and ketones via vinylogous ¹⁸F-fluorination of ?-diazoacetates with [¹⁸F]AgF.

ABSTRACT: This communication reports a method for the vinylogous radiofluorination of ?-diazoacetates to generate ?-[¹⁸F]fluoro-?,?-unsaturated esters and ketones in moderate to good radiochemical yields. The method uses no-carrier-added [¹⁸F]AgF and is compatible with aromatic and non-aromatic substrates and a number of different functional groups. The labeling method is showcased in the synthesis of a fluorinated 5-cholesten-3-one derivative as well as a difluorinated product pertinent to drug discovery.

SUBMITTER: Thompson S

PROVIDER: S-EPMC7328919 | biostudies-literature | 2019 Dec

REPOSITORIES: biostudies-literature

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Synthesis of [18F]-γ-fluoro-α,β,-unsaturated esters and ketones via vinylogous 18F-fluorination of α-diazoacetates with [18F]AgF.

Thompson Stephen S Lee So Jeong SJ Jackson Isaac M IM Ichiishi Naoko N Brooks Allen F AF Sanford Melanie S MS Scott Peter J H PJH

Synthesis 20191201 23

This communication reports a method for the vinylogous radiofluorination of α-diazoacetates to generate γ-[18F]fluoro-α,β-unsaturated esters and ketones in moderate to good radiochemical yields. The method uses no-carrier-added [18F]AgF and is compatible with aromatic and non-aromatic substrates and a number of different functional groups. The labeling method is showcased in the synthesis of a fluorinated 5-cholesten-3-one derivative as well as a difluorinated product perti ...[more]

PMID: 32612311

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