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

Synthesis of Novel Chiral 7-Amide Substituted-4-androstene-3,17-dione Derivatives
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摘要 A series of novel 7-amide substituted-4-androstene-3,17-dione derivatives(8αa "8αh or 8βa "8βh) was synthesized from the important intermediates 5 by N-acylation and acidic hydrolysis.Compounds 5α 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(hetero-nuclear multiple quantum coherence) and NOE(nuclear overhauser effect) correlation. A series of novel 7-amide substituted-4-androstene-3,17-dione derivatives(8αa "8αh or 8βa "8βh) was synthesized from the important intermediates 5 by N-acylation and acidic hydrolysis.Compounds 5α 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(hetero-nuclear multiple quantum coherence) and NOE(nuclear overhauser effect) correlation.
出处 《Chemical Research in Chinese Universities》 SCIE CAS CSCD 2011年第4期604-609,共6页 高等学校化学研究(英文版)
基金 Supported by the National Natural Science Foundation of China(No.20576094)
关键词 ANDROSTENEDIONE Allylic oxidation Reduction N-ACYLATION Androstenedione Allylic oxidation Reduction N-Acylation
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