Oxandrolone: Oxandrolone, 17/i-hydroxy-17a-methyl-2-oxa-5-androstan-3-one (29.3.10), is made by oxidation of the C1-C2 double bond of 17/i-hydroxy-17a-methyl-1-androsten-3-one by a mixture of lead tetraacetate and osmium tetroxide with an opening of the A ring of the steroid system, which forms an aldehyde acid (29.3.9). Upon reducing the aldehyde group with sodium borohydride, intramolecular cyclization takes place, directly forming a lactone (29.3.10), which is the desired oxandrolone [31,32].
Stanozol: Stanozol, 17a-methyl-5a-androstano[3,2-c]pyrazol-17/i-ol (29.3.13), is made by reducing the double bond at C4-C5 in methyltestosterone, which has independent interest as an anabolic drug of mestanolone (29.3.11). Mestanolone undergoes formylation with ethylformate in the presence of sodium ethoxide, forming a 2-formyl (oxymethylene) derivative (29.3.12), which upon reaction with hydrazine easily cyclizes to the desired stanazole (29.3.13), which is a pyrazol-condensed steroid system [33,34].
h3c oh h3c oh h3c oh
HCOOC2H5/ C2H5ONa OH H3C
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