Syntheses of large ring hormone analogs Public Deposited

http://ir.library.oregonstate.edu/concern/graduate_thesis_or_dissertations/x920g0693

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  • The (±) 8,9:13,14-diseco-norestradiol, a large ring hormone analog, and its related derivatives, were prepared by a ring expansion approach. The key step of this approach is the establishment of the benzocyclododecenone system via the Caubere reaction. This step not only provides a favorable ring size, it also sets the necessary functionalities in their desired positions. The intermediate benzocyclodecenone was further expanded to the required thirteen membered ring skeleton via the Tiffeneau-Demyanov rearrangement. Reduction of the carbonyl followed by demethylation of the intermediate dimethyl ether yielded the large ring hormone analog. In addition to the synthesis of the estradiol analog, methods directed towards the preparation of another large ring hormone analog, the 5,10:8,9-diseco steroid, were also investigated. The key intermediate is the 7-methoxy-4'-oxocyclohexenodecene, which conceivably can be cleaved by ozonolysis to generate the fourteen-membered ring with the essential oxygen functionalities in their desired positions. This intermediate was also employed as a starting material for the synthesis of the 5,10-seco, C-ring aromatic hormone analog, 4'-acety1- 7-methoxy-1,2-benzocyclodecene.
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