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An improved preparation of 3-α-acetoxy-11,20-diketo-(5β)-pregnane, the key intermediate in the synthesis of 11-oxygenated corticosteroids.

✍ Scribed by M. Stefanović; M. Gašić; J. Hranisavljević; M. Đermanović

Publisher
Elsevier Science
Year
1967
Tongue
French
Weight
180 KB
Volume
8
Category
Article
ISSN
0040-4039

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✦ Synopsis

Although microbiological methods of introducing oxygen at C-11 of the steroid molecule are effeotive, it ie obvious that purely synthetic waya of producing cortieone and its analoguea from bile acids or hecogenin have never been abondoned. Thus, we suooeeded to obtain 3aLacetory-11,2& diketo-(5 &)-pregnane XI, the key intermediate in the syntheeie of 11-oxygenated oortiooeteroida in a very improved yield exceeding 13% oalaulated on etarting deamhollo acid I by the following sequence of reactions:

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The conversion ofdesoxycholic acid (2) into the title compound 14 by 13 respectively 17 steps is described herein, including stereoselective construction of C-3 and C-6 hydroxy moieties and introduction of a A 9"lj double bond by dehydrogenation. 14 is believed to serve as a putative precursor for t