D.Sc. (Chemistry) / Please refer to full text to view abstract

183, xii leaves : ill. / Title page, contents and abstract only. The complete thesis in print form is available from the University Library. / Thesis (Ph.D.)--University of Adelaide, Dept. of Obstetrics and Gynaecology, 1969

Thesis (Ph.D.)--University of Adelaide, Dept. of Obstetrics and Gynaecology, 1969.

Thesis (Ph. D.)--University of Wisconsin--Madison, 1954. / Typescript. Vita. eContent provider-neutral record in process. Description based on print version record. Includes bibliographical references (leaves 128-132).

Thesis (Ph. D.)--University of Wisconsin--Madison, 1945. / Typescript. Vita. eContent provider-neutral record in process. Description based on print version record. Includes bibliographical references.

Ozonization of 7-ketocholesteryl acetate has yielded methyl 5-keto-5, 7-seco-6-nor-3-cholestene-7-oate in reasonably high yield. This intermediate was converted by catalytic hydrogenation to methyl-5-keto-5, 7-seco-6-norcholestan-7-oate which upon treatment with benzyl amine gave N-benzyl-6-aza-4-cholesten-7-one. / Science, Faculty of / Chemistry, Department of / Graduate

A sequence leading to the total synthesis of cis-syn-cis-dodecahydrochrysene and cis-octahydrochrysene derivatives is described. The synthesis employs the Robinson-Mannich base reaction and the Michael reaction to construct the tetracyclic skeleton. Condensation of 6-methoxy-2-tetralone with 1-diethylamino-3-pentanone methiodide affords an isomeric mixture of tricyclic ketones. This mixture is then condensed with methyl vinyl ketone to yield 1β,6-dimethyl-6-hydroxy-2,3-(2'-methoxy-7',8'-dihydro-6',5'-naphtho)-Δ² -bicyclo [3.3. 1] nonene-9-one (IV). By appropriate modifications this compound can then be utilized for the synthesis of a variety of hydrochrysene analogues. Oxidation of dodecahydrochrysenes with t-butyl chromate solution is found to be dependent on the stereochemistry of the molecule. Whereas trans-anti-trans-2-methoxy-8β -acetoxy-10a-methyl-4b, 5,6,6a, 7,8,9,10,10a,10b,11,12-dodecahydrochrysene (XVIII) gives the 12-keto derivative XIX, cis-syn-cis-2-methoxy-8α-acetoxy-10a-methyl-4b,5,6,6a,7,8,9,10,10a,10b,11,12-dodecahydrochrysene (XVII) yields cis-2-methoxy-8α -acetoxy-5-keto-10a-methyl-5,6,6a, 7,8,9,10,10a-octahydrochrysene (XXIV). In the latter reaction, t-butyl chromate is superior to chromium trioxide as an oxidizing agent. Nuclear magnetic resonance spectra are found to be invaluable for the purpose of characterization of these rather complex molecules. / Science, Faculty of / Chemistry, Department of / Graduate

The Beckmann rearrangement of the oxime of 11-oxo-⍺, 20-dihydroxy-C-nor pregnane (54) provided the corresponding lactam (56). Oxidation of the latter with Jones reagent furnished the 3-keto-alcohol (57), which upon its conversion to the acetate derivative (58) followed by bromination and dehydrobromination yielded ll-aza-20-acetoxy-pregn-4-ene-3,12-dione (60). Hydrolysis of the latter to the ∆⁴ -3-keto alcohol (62) followed by oxidation furnished the desired ll-aza-pregn-4-ene-3,12,20-trione (63). The synthetic sequence provides the first examples of ll-aza steroid analogues in which ring C is a six membered and ring A possesses the ∆⁴-3-keto moiety. / Science, Faculty of / Chemistry, Department of / Graduate

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