Steroids p. 475 - 484 (1983)
Update date:2022-08-11
Topics:
Leppik, Raymond A.
Cholic and deoxycholic acids can be converted into 3-keto derivatives in 75-80percent yield, by a four-step synthesis consisting of formylation, selective deformylation of the 3-formoxyl group, oxidation, then deformylation of the remaining formoxyl groups.The intermediate 3-keto formoxyl acids in this sequence were shown to be suitable starting compounds for the synthesis of 4-ene-3-keto acids, in 55-60percent yield, via bromination, dehydrobromination, and deformylation.By extending the dehydrobromination reaction, the 7α-formoxyl group of the intermediate 4-ene-3-keto-7α,12α-diformoxyl acid is also lost, hence providing a useful synthetic route to 4,6-diene-3-keto bile acids.
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Doi:10.1016/j.ica.2021.120357
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(1970)
