STEROIDS AND RELATED PRODUCTS: XI. THE SYNTHESIS OF 3,9,12,20-TETRAOXYGENATED 9,12-SECO-STEROIDS. PART I
- 1 December 1959
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 37 (12) , 2031-2041
- https://doi.org/10.1139/v59-295
Abstract
The synthesis of 3α,20β-dihydroxy-9-oxo-9,12-seco-12-pregnanoic acid (XV) and some of its derivatives, from 3α,12α-diacetoxy-20-oxopregnane, is described. The fission of ring C was achieved by ozonolysis of a 9,11-unsaturated 12-ketones. In the course of this work evidence was found that the rearrangement of certain 11-hydroxy-12-ketones to 12β-hydroxy-11-ketones, under the influence of alkali, can occur in high yield, even at room temperature.Keywords
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