Development of a novel geminal-difluorination method and its application in the synthesis of sup 18 F-labeled fatty acid analogues as potential myocardial imaging agents
An efficient two-step fluorination procedure for transforming a ketone or aldehyde to the corresponding gem-difluoro compound has been developed. The gem-difluoro compounds can be prepared by first forming the corresponding 1,3-dithiolane followed by reaction with 1,3-dibromo-5,5-dimethylhydantoin and pyridinium poly(hydrogen fluoride). The reaction requires 2 equivalents of Br{sup +} and appears to proceed through a sequence of two bromosulfonium ions that open and cleave, respectively, to sulfur- and fluorine-stabilized carbocations that are trapped by fluoride ion. A convenient, general synthetic route to functionalized fatty acids has been developed and utilized in the synthesis of (16-{sup 18}F),6,6-trifluorohexadecanoic acid and (16-{sup 18}F)7,7-trifluorohexadecanoic acid as potential myocardial imaging agents. Corey's 2-lithio-1,3-dithiane methodology was employed both to link two terminally difunctionalized carbon chains, thereby producing the fatty acid precursor, and to introduce the 1,3-dithiane which would ultimately become a gem-difluoromethylene group.
- Research Organization:
- Illinois Univ., Urbana, IL (USA)
- OSTI ID:
- 7245572
- Country of Publication:
- United States
- Language:
- English
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62 RADIOLOGY AND NUCLEAR MEDICINE
BETA DECAY RADIOISOTOPES
BETA-PLUS DECAY RADIOISOTOPES
BODY
CARBOXYLIC ACIDS
CARDIOVASCULAR SYSTEM
CHEMICAL PREPARATION
DRUGS
FLUORINE 18
FLUORINE ISOTOPES
HEART
HOURS LIVING RADIOISOTOPES
IMAGE PROCESSING
ISOMERIC TRANSITION ISOTOPES
ISOTOPES
LABELLED COMPOUNDS
LIGHT NUCLEI
MUSCLES
MYOCARDIUM
NUCLEI
ODD-ODD NUCLEI
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANS
PRECURSOR
PROCESSING
RADIOISOTOPES
RADIOPHARMACEUTICALS
SYNTHESIS