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Title: The synthesis and structure elucidation of organotin-steroids
Author: Buchanan, H. J.
Awarding Body: University of Aberdeen
Current Institution: University of Aberdeen
Date of Award: 1997
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The thesis was concerned with the synthesis structures and activity and reactivities of stannylated steroid derivatives. Most attention has been paid to cholesterol and cholestene derivatives. Directly bonded stannylated cholestene derivatives have been obtained by various routes. 3α-triphenylstannylcholest-5-ene was obtained from the regiospecific reaction of Ph3SnLi with cholesteryl sulphonates; 3β-triorganostannylcholest-5-ene was obtained by the regiospecific reaction of Ph3SnCl with 3β-chloromagnesiocholest-5-ene. The Barbieri-type reaction of Ph3SnCl and 3β-chlorocholest-5-ene gave both the 3α- and 3β- phenylstannylcholest-5-enes. Compounds with different linkages between the organostannyl and cholestene moieties were also obtained e.g. 3β-(Ph3Sn)-CH2O-(cholest-5-ene), 3β-(Ph3Sn)-CH2CH2CH2O-(cholest-5-ene) and (Ph3Sn)-CH2CH2CO2-(cholest-5-ene). However compounds could not be made with the following linkages, (Ph3Sn)-CH2CH2CO-(cholest-5-ene) or (Ph3Sn)-O-cholest-5-ene. The preparation of these indirectly bonded stannyl cholestenes utilised various reactions including (i) nucleophilic substitution of organostannyl halides with the C-3 hydroxyl group of the steroid, (ii) addition of organotin hydrides across alkenyl systems. Phenyl-tin bond cleavage in all the stannylated steroids was attempted using iodine to produce mono and diiodo derivatives. All products were characterised by solution NMR (1H, 13C and 119Sn) spectra and in some cases, e.g. 3α-triphenylstannylcholest-5-ene, 3α-iododiphenylstannyl)cholest-5-ene, 3α-(diiodophenylstannyl)cholest-5-ene and 3α-(triphenylstannylmethoxy)cholest-5-ene, by X-ray crystallography. Some initial testing of the compounds as anti-cancer agents has been carried out: the results were not encouraging.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available