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

高等学校化学研究 ›› 2011, Vol. 27 ›› Issue (4): 604-609.

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

CHEN Shao-rui^1,2, ZHOU Xue-qin¹, LI Wei¹ and LIU Dong-zhi^1*

1. School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072, P. R. China;
2. College of Science, Hebei University of Science and Technology, Shijiazhuang 050018, P. R. China

收稿日期:2010-09-03 修回日期:2010-11-08 出版日期:2011-07-25 发布日期:2011-06-29
通讯作者: LIU Dong-zhi E-mail:dzliu@tju.edu.cn
基金资助:
Supported by the National Natural Science Foundation of China(No.20576094).

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

CHEN Shao-rui^1,2, ZHOU Xue-qin¹, LI Wei¹ and LIU Dong-zhi^1*

1. School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072, P. R. China;
2. College of Science, Hebei University of Science and Technology, Shijiazhuang 050018, P. R. China

Received:2010-09-03 Revised:2010-11-08 Online:2011-07-25 Published:2011-06-29
Contact: LIU Dong-zhi E-mail:dzliu@tju.edu.cn
Supported by:
Supported by the National Natural Science Foundation of China(No.20576094).

摘要/Abstract

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.

关键词: Androstenedione, Allylic oxidation, Reduction, N-Acylation

Abstract: 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.

Key words: Androstenedione, Allylic oxidation, Reduction, N-Acylation

CHEN Shao-rui, ZHOU Xue-qin, LI Wei and LIU Dong-zhi*. Synthesis of Novel Chiral 7-Amide Substituted-4-androstene-3,17-dione Derivatives[J]. 高等学校化学研究, 2011, 27(4): 604-609.

CHEN Shao-rui, ZHOU Xue-qin, LI Wei and LIU Dong-zhi*. Synthesis of Novel Chiral 7-Amide Substituted-4-androstene-3,17-dione Derivatives[J]. Chemical Research in Chinese Universities, 2011, 27(4): 604-609.

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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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