Efficient Synthesis of 2-Ethyl-A-ring Analogues of 19-Nor-1α,25-dihydroxy Vitamin D3

高等学校化学研究 ›› 2003, Vol. 19 ›› Issue (2): 165-173.

Efficient Synthesis of 2-Ethyl-A-ring Analogues of 19-Nor-1α,25-dihydroxy Vitamin D₃

WANG Qiuan¹, ZHAO Yu-rui²

1. College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. China;
2. Department of Organic Chemistry, University of Gent, Krijgslaan 281 S4, B-9000 Gent, Belgium

收稿日期:2002-04-02 出版日期:2003-04-24 发布日期:2011-08-06

Efficient Synthesis of 2-Ethyl-A-ring Analogues of 19-Nor-1α,25-dihydroxy Vitamin D₃

WANG Qiuan¹, ZHAO Yu-rui²

1. College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. China;
2. Department of Organic Chemistry, University of Gent, Krijgslaan 281 S4, B-9000 Gent, Belgium

Received:2002-04-02 Online:2003-04-24 Published:2011-08-06

摘要/Abstract

摘要： The novel 19-nor-lα,25-dihydroxy vitamin D3 analogues possessing an ethyl at the 2-position(4 and 5), were synthesized by coupling 25-hydroxy Windaus-Grundmann ketone derivative 20 with A-ring synthons(15 and 19) respectively. The enantioselective synthesis of substituted bicyclic[3,1,0] hexanes structure A-ring synthons, started from all-cis-3,5-dihydroxy-4-ethyl-1-(methoxycarbonyl)cyclohexane via lipase-catalyzd asymmetrization, was demonstrated.

关键词: 2-Ethyl-19-nor-1&alpha, 25-dihydroxy vitamin D₃, Synthesis, Lipase-catalyzed, Asymmetrization

Abstract: The novel 19-nor-lα,25-dihydroxy vitamin D3 analogues possessing an ethyl at the 2-position(4 and 5), were synthesized by coupling 25-hydroxy Windaus-Grundmann ketone derivative 20 with A-ring synthons(15 and 19) respectively. The enantioselective synthesis of substituted bicyclic[3,1,0] hexanes structure A-ring synthons, started from all-cis-3,5-dihydroxy-4-ethyl-1-(methoxycarbonyl)cyclohexane via lipase-catalyzd asymmetrization, was demonstrated.

Key words: 2-Ethyl-19-nor-1α,25-dihydroxy vitamin D₃, Synthesis, Lipase-catalyzed, Asymmetrization

WANG Qiuan, ZHAO Yu-rui. Efficient Synthesis of 2-Ethyl-A-ring Analogues of 19-Nor-1α,25-dihydroxy Vitamin D₃[J]. 高等学校化学研究, 2003, 19(2): 165-173.

WANG Qiuan, ZHAO Yu-rui. Efficient Synthesis of 2-Ethyl-A-ring Analogues of 19-Nor-1α,25-dihydroxy Vitamin D₃[J]. Chemical Research in Chinese Universities, 2003, 19(2): 165-173.

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Efficient Synthesis of 2-Ethyl-A-ring Analogues of 19-Nor-1α,25-dihydroxy Vitamin D₃

Efficient Synthesis of 2-Ethyl-A-ring Analogues of 19-Nor-1α,25-dihydroxy Vitamin D₃

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