Recognition of D-homoannulation by proton and carbon NMR spectra.
One-and two dimensional proton and carbon NMR spectra of the D-homoannulated rearrangement product of triamcinolone (9 alpha-fluoro-11 beta,16 alpha,17 alpha, 21-tetrahydroxy-pregna-1,4-diene-3,20-dione) establish its structure as that of 9 alpha-fluoro-11 beta,16 alpha,17 alpha-trihydroxy-17 beta-hydroxy-methyl-D-homoandrosta-1,4-diene-3,17 alpha-dione. These methods accord ready recognition of D-homoannulation of C21-17-hydroxy-20-ketosteroids.
Smith
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LL
Department of Human Biological Chemistry and Genetics, University of Texas Medical Branch, Galveston 77550.
Ezell
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EL
D000737:Androstenols / Q000032:analysis; D002247:Carbon Isotopes; D055598:Chemical Phenomena; D002621:Chemistry; D006718:Homosteroids / Q000032:analysis; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D011522:Protons; D014221:Triamcinolone / Q000032:analysis*
D000737:Androstenols; D002247:Carbon Isotopes; D006718:Homosteroids; D011522:Protons; C061543:9-fluoro-11,16,17-trihydroxy-17-hydroxymethyl-D-homoandrosta-1,4-diene-3,17-dione; C061544:16-acetoxy-17-acetoxymethyl-11,17-dihydroxy-D-homoandrosta-1,4-diene-3,17-dione; D014221:Triamcinolone