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

被引:0
|
作者
WANG Qiu an 1
2. Department of Organic Chemistry
机构
关键词
Ethyl; 19; nor; α; 25 dihydroxy vitamin D 3; Synthesis; Lipase catalyzed; Asymmetrization;
D O I
暂无
中图分类号
TQ466 [维生素制造];
学科分类号
摘要
The novel 19 nor l α ,25 dihydroxy vitamin D 3 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 hexanes structure A ring synthons, started from all cis 3,5 dihydroxy 4 ethyl 1 (methoxycarbonyl)cyclohexane via lipase catalyzd asymmetrization, was demonstrated.
引用
收藏
页码:165 / 173
页数:9
相关论文
共 50 条
  • [41] 1α,25-dihydroxy-3-epi-vitamin D3, a natural metabolite of 1α,25-dihydroxy vitamin D3:: production and biological activity studies in pulmonary alveolar type II cells
    Rehan, VK
    Torday, JS
    Peleg, S
    Gennaro, L
    Vouros, P
    Padbury, J
    Rao, DS
    Reddy, GS
    MOLECULAR GENETICS AND METABOLISM, 2002, 76 (01) : 46 - 56
  • [42] Mechanism of Pdia3-dependent 1α,25-dihydroxy vitamin D3 signaling in musculoskeletal cells
    Boyan, Barbara D.
    Chen, Jiaxuan
    Schwartz, Zvi
    STEROIDS, 2012, 77 (10) : 892 - 896
  • [43] Transcriptional control of intestinal cytochrome P-4503A by 1α,25-dihydroxy vitamin D3
    Thummel, KE
    Brimer, C
    Yasuda, K
    Thottassery, J
    Senn, T
    Lin, Y
    Ishizuka, H
    Kharasch, E
    Schuetz, J
    Schuetz, E
    MOLECULAR PHARMACOLOGY, 2001, 60 (06) : 1399 - 1406
  • [44] Effect of 1α,25-Dihydroxy Vitamin D3 on Proliferation and Differentiation of C2C12 Myoblast
    Oktuno, H.
    Kishimoto, K. N.
    Hatori, M.
    Itoi, E.
    JOURNAL OF BONE AND MINERAL RESEARCH, 2008, 23 : S180 - S180
  • [45] Synthesis, Conformational Analysis, and Biological Evaluation of 19-nor-Vitamin D3 Analogues with A-Ring Modifications
    Sanchez-Abella, Laura
    Fernandez, Susana
    Verstuyf, Annemieke
    Verlinden, Lieve
    Gotor, Vicente
    Ferrero, Miguel
    JOURNAL OF MEDICINAL CHEMISTRY, 2009, 52 (19) : 6158 - 6162
  • [46] A practical synthesis of 14-epi-19-nor-1a,25-dihydroxyvitamin D3 analogues and their A-ring epimers
    Wu, YS
    Zhao, YR
    Tian, HJ
    De Clercq, P
    Vandewalle, M
    Berthier, M
    Pellegrino, G
    Maillos, P
    Pascal, JC
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2001, 2001 (20) : 3779 - 3788
  • [47] Design and efficient synthesis of new stable 1α,25-dihydroxy-19-norvitamin D3 analogues containing amide bond
    Suhara, Y
    Kittaka, A
    Ono, K
    Kurihara, M
    Fujishima, T
    Yoshida, A
    Takayama, H
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (24) : 3533 - 3536
  • [48] Expression of 1,25-dihydroxy vitamin D3 receptor in breast carcinoma
    Friedrich, M
    Rafi, L
    Tilgen, W
    Schmidt, W
    Reichrath, J
    JOURNAL OF HISTOCHEMISTRY & CYTOCHEMISTRY, 1998, 46 (11) : 1335 - 1337
  • [49] Efficient and Versatile Synthesis of A-Ring Precursors of 1a,25-Dihydroxy-vitamin D3 and Analogues. Application to the Synthesis of Lythgoe-Roche Phosphine Oxide
    MouriOo, A.
    Torneiro, M.
    Vitale, C.
    Fernandez, S.
    Tetrahedron Letters, 38 (26):
  • [50] Effect of 1α,25-dihydroxy vitamin D3 and vitamin E on insulin-induced glucose uptake in rat adipocytes
    Huang, YN
    Ishizuka, T
    Miura, A
    Kajita, K
    Ishizawa, M
    Kimura, M
    Yamamoto, Y
    Kawai, Y
    Morita, H
    Uno, Y
    Yasuda, K
    DIABETES RESEARCH AND CLINICAL PRACTICE, 2002, 55 (03) : 175 - 183