Cramp, Michael Colin (1982) Some aspects of organic synthesis. University of Southampton, Doctoral Thesis.
Abstract
New synthetic methods are always of importance in organic chemistry allowing new routes for total syntheses. Chapter I is concerned with the preparation of the dihydroxyacetone side-chaincharacteristic of adriamycin and some cortico-steroids. A route via the dianion of 2-phenylthioethanol was investigated. Chapter II deals with two novel annulation procedures. Firstly 3-phenylthiobut-3-en-2-one was prepared and its use as an annulatingagent studied. Secondly the reaction between 4-chlorobutan-2-one and the sodium enolate of 2-phen;lthiocyclohexanone was investigated, leading, subsequently, to a variety of cyclic products, some of which were aromatic. Chapter III includes the catalyzed rearrangement of propargyl acetates to allenyl and 1,3-dienyl acetates and some Diels-Alder reactions of the latter. Finally the preparation of 5,6-dihydro-6pentyl-2H-pyran-2-one, a substitute for coumarin in the perfumery industry, via a rearrangement involving an allene, is discussed.
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