Part I. Aromatic Fluorinations for Fluorine-18 Labeling of Estrogens. Part Ii. Bromodesilylation-Potential Method for Regiospecific Radiobromination of Aromatic Systems. Part Iii. Synthesis of Isohexestrol and Isohexestrol Derivatives
Ng, Johny Sau-Hoi
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https://hdl.handle.net/2142/70165
Description
Title
Part I. Aromatic Fluorinations for Fluorine-18 Labeling of Estrogens. Part Ii. Bromodesilylation-Potential Method for Regiospecific Radiobromination of Aromatic Systems. Part Iii. Synthesis of Isohexestrol and Isohexestrol Derivatives
Author(s)
Ng, Johny Sau-Hoi
Issue Date
1981
Department of Study
Chemistry
Discipline
Chemistry
Degree Granting Institution
University of Illinois at Urbana-Champaign
Degree Name
Ph.D.
Degree Level
Dissertation
Keyword(s)
Chemistry, Organic
Abstract
Two aromatic fluorination methods, the decomposition of aryl azides and the decomposition of aryl triazenes, were investigated as methods potentially suitable for fluorine-18 labeling of estrogens. The aryl triazene method gives moderate yields in many systems, but fails with ortho methoxy or methanesulfonyloxy groups. The aryl azide method gives good yields of p-fluoroanilines, which can be deaminated readily, but oxygen or large alkyl groups ortho to the azide interfere with the fluorination. The synthesis of meta-fluorohexestrol, a non-steroidal estrogen with high binding affinity for the estrogen receptor, was achieved via the aryl triazene decomposition method. This method was also extended to aromatic bromination in the synthesis of meta-bromohexestrol.
Bromodesilylation, a potentially useful method for radiobromination of estrogens, was investigated in a model system. Meta-bromophenyltrifluoromethanesulfonate was synthesized from the corresponding meta-trimethysilyl derivative in a clean bromodesilylation reaction.
The total syntheses of isohexestrol (erythro 3-(3'-hydroxyphenyl)-4-(4'-hydroxyphenyl)hexane) and its derivatives are reported. The relative binding affinities of these compounds to estrogen receptor are investigated.
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