Ozonization of Ʒβ, 20β -diacetoxy-5-pregnene-7-one (XII) gave methyl Ʒβ ,20β -diacetoxy-5-oxo-5,7-seco-6-norpregnan-7-oate (XIII). Treatment of the latter with sodium hydroxide yielded methyl 20β -acetoxy-5-oxo-5,7-seco-6-nor-Ʒ-pregnen-7-oate (XIV), which upon reduction gave methyl 20β -acetoxy-5-oxo-5,7-seco-6-norpregnan-7-oate (XV) in high yield (see Figure 20).
Upon treatment of the latter with benzylamine, ring closure occurred and the enol lactam, 20β -acetoxy-N-benzyl-6-aza-4-pregnen-7-one (XVI) was formed. Catalytic reduction of the double bond followed by reduction of the carbonyl with lithium aluminum hydride yielded 20β -hydroxy-N-benzyl-6-aza-5§ -pregnane (XVIII) . / Science, Faculty of / Chemistry, Department of / Graduate
| Identifer | oai:union.ndltd.org:UBC/oai:circle.library.ubc.ca:2429/38204 |
| Date | January 1965 |
| Creators | Gletsos, Constantine |
| Publisher | University of British Columbia |
| Source Sets | University of British Columbia |
| Language | English |
| Detected Language | English |
| Type | Text, Thesis/Dissertation |
| Rights | For non-commercial purposes only, such as research, private study and education. Additional conditions apply, see Terms of Use https://open.library.ubc.ca/terms_of_use. |
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