This thesis is concerned with an approach to the synthesis of the C/D ring system and side chain of steroids with 11-oxygen functionality. (+)-9,10-Dibromocamphor (18) [prepared in three steps from (+)-endo-3-bromocamphor (4)] was converted to the diester 144 in six steps. The diester 144 underwent a modified acyloin reaction to provide the silylated enediolate 154. A novel methanolysis of the acyloin intermediate 154 gave a 1:1 mixture of the isomeric tricyclic methoxy-ketones 168 and 176. Oxidative cleavage of these methoxyketones 168
[Formula Omitted]
and 176 provided the isomeric aldehydes 178 and 180 which were then transformed into the corresponding isomeric esters 181 and 182. This represents a synthesis of the C/D ring system of steroids with 11-oxygen functionality and establishment of the correct absolute stereochemistry at C(13) and C(17).
[Formula Omitted] / Science, Faculty of / Chemistry, Department of / Graduate
| Identifer | oai:union.ndltd.org:UBC/oai:circle.library.ubc.ca:2429/26512 |
| Date | January 1987 |
| Creators | Pendleton, Nevil |
| 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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