H. Brodie, C. Hay, J. D. Townsley
Jun 8, 1971
Citations
0
Influential Citations
4
Citations
Journal
Biochimica et biophysica acta
Abstract
Abstract 1. 1. We have confirmed the observation that incubation of 17β-hydroxyestr-4-en-3-one 1a with Botrodiplodia malorum yields almost exclusively the corresponding 1β-hydroxy compound. 2. 2. However, when estr-4-ene-3,17-dione 1b was incubated under the same conditions we found that the major product was 7β-hydroxyestr-4-ene-3,17-dione, obtained in 30–40% yield. Proof of structure and physical and chemical properties of this compound and the corresponding acetate are reported. 3. 3. Only a 3% yield of 1β-hydroxyestr-4-ene-3,17-dione was obtained. 4. 4. The other mono-oxygenated products isolated were 6β-hydroxyestr-4-ene-3,17-dione (10% yield) and estr-4-ene-3,11,17-trione (3% yield). 5. 5. Small amounts of many apparently poly-hydroxylated Δ4-3-ketones were also formed; one of these was tentatively identified as 7β,11β-dihydroxyestr -4-ene-3,17-dione. 6. 6. The transformations are discussed from the standpoint that an enzyme could mediate hydroxylation at more than one site. 7. 7. Syntheses of 6β-hydroxyestr-4-ene-3,17-dione, the corresponding 6β-acetate, estr-4-ene-3,6,17-trione, 17β-hydroxyestra-4,6-dien-3-one and estra-4,6-diene-3,17-dione are presented.