Synthesis of 16-fluoroestrogens by unusually facile fluoride ion displacement reactions: prospects for the preparation of fluorine-18 labeled estrogens

Journal Article · Fri Dec 14 04:00:00 EST 1984 · J. Org. Chem.; (United States)

DOI:https://doi.org/10.1021/jo00199a031· OSTI ID:5838111

Kiesewetter, D O; Katzenellenbogen, J A; Kilbourn, M R; Welch, M J

16..cap alpha..-Fluoroestradiol and 16..beta..-fluoroestradiol can be prepared by the reaction of fluoride ion with the opposite corresponding epimeric (((trifluoromethyl)sulfonyl)oxy)estrone precursors, followed by stereoselective reduction to the 17..beta..-estradiols. The related 17..beta..-ethynyl compounds can be prepared by ethynylation of the fluoroestrones. Stereochemical assignments, suggested by known reaction stereoselectivities, are supported by extensive /sup 1/H and /sup 19/F NMR analyses. The fluoride ion displacement reactions operate rapidly and efficiently at room temperature, even with low concentrations of fluoride ion. This rapid and convenient fluorination method is adaptable to the preparation of fluorine-18 labeled estrogens that may be useful as breast tumor imaging agents. 18 references, 1 tables.

• Research Organization: Univ. of Illinois, Urbana
• DOE Contract Number: FG02-84ER60218
• OSTI ID: 5838111
• Journal Information: J. Org. Chem.; (United States), Journal Name: J. Org. Chem.; (United States) Vol. 49:25; ISSN JOCEA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400301* -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)
550601 -- Medicine-- Unsealed Radionuclides in Diagnostics
62 RADIOLOGY AND NUCLEAR MEDICINE
CHEMICAL PREPARATION
DATA
DRUGS
EFFICIENCY
ESTROGENS
EXPERIMENTAL DATA
HORMONES
INFORMATION
NMR SPECTRA
NUMERICAL DATA
ORGANIC COMPOUNDS
ORGANIC FLUORINE COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
SPECTRA
STEREOCHEMISTRY
STEROID HORMONES
STRUCTURAL CHEMICAL ANALYSIS
SYNTHESIS