Synthesis of Novel Chiral 7-Amide Substituted-4-androstene-3,17-dione Derivatives

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A series of novel 7-amide substituted-4-androstene-3,17-dione derivatives(8βαa-8αh or 8βa-8βh) was synthesized from the important intermediates 5 by N-acylation and acidic hydrolysis.Compounds 5a and 5β were obtained through the reaction sequence including acetalization,allylic oxidation,oximation and reduction.The structures of the target compounds were characterized by MS,1H NMR,13C NMR and HRMS spectra and their stereo configurations were identified through DEPT(distortionless enhancement by polarization transfer),HMQC(heteronuclear multiple quantum coherence) and NOE(nuclear overhauser effect) correlation.
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