Efficient convergent synthesis of 1α,25-dihydroxyvitamin D3 and its analogues by Suzuki-Miyaura coupling

被引:20
|
作者
Hanazawa, T [1 ]
Koyama, A [1 ]
Wada, T [1 ]
Morishige, E [1 ]
Okamoto, S [1 ]
Sato, F [1 ]
机构
[1] Tokyo Inst Technol, Grad Sch Biosci & Biotechnol, Midori Ku, Yokohama, Kanagawa 2268501, Japan
关键词
D O I
10.1021/ol0274007
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] 1alpha,25-Dihydroxyvitamin D-3 was synthesized by the Suzuki-Miyaura coupling of the A-ring intermediate 1, which was efficiently prepared from readily available 1,7-enyne 2, with the corresponding boronate compound of the C,D-ring portion. The method was applied to prepare des-C,D analogues of 1alpha,25-dihydroxyvitamin D-3.
引用
收藏
页码:523 / 525
页数:3
相关论文
共 50 条
  • [11] Efficient and versatile synthesis of novel 2α-substituted 1α,25-dihydroxyvitamin D3 analogues and their docking to vitamin D receptors
    Suhara, Y
    Nihei, K
    Kurihara, M
    Kittaka, A
    Yamaguchi, K
    Fujishima, T
    Konno, K
    Miyata, N
    Takayama, H
    JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (26): : 8760 - 8771
  • [12] An Expeditious Route to 1α,25-Dihydroxyvitamin D3 and Its Analogues by an Aqueous Tandem Palladium-Catalyzed A-Ring Closure and Suzuki Coupling to the C/D Unit
    Gogoi, Pranjal
    Sigueiro, Rita
    Eduardo, Silvina
    Mourino, Antonio
    CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (05) : 1432 - 1435
  • [13] Efficient synthesis of symmetrically and unsymmetrically substituted hexaphenylbenzene analogues by Suzuki-Miyaura coupling reactions
    Yang, Xiaoyin
    Don, Xi
    Muellen, Klaus
    CHEMISTRY-AN ASIAN JOURNAL, 2008, 3 (04) : 759 - 766
  • [14] Differential apoptotic response of human melanoma cells to 1α,25-dihydroxyvitamin D3 and its analogues
    Carina Danielsson
    Karin Fehsel
    Patsie Polly
    Carsten Carlberg
    Cell Death & Differentiation, 1998, 5 : 946 - 952
  • [15] Differential apoptotic response of human melanoma cells to 1α,25-dihydroxyvitamin D3 and its analogues
    Danielsson, C
    Fehsel, K
    Polly, P
    Carlberg, C
    CELL DEATH AND DIFFERENTIATION, 1998, 5 (11): : 946 - 952
  • [16] Synthesis of an intermediate for A-ring of 19-nor-1α,25-dihydroxyvitamin D3 analogues
    Wu, Y
    Guan, M
    Ji, T
    Cheng, L
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2001, 40 (02): : 136 - 138
  • [17] Synthesis and preliminary biological evaluation of new antiproliferative aromatic analogues of 1α,25-dihydroxyvitamin D3
    Thomas, Emmanuel
    Brion, Jean-Daniel
    Peyrat, Jean-Francois
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2014, 86 : 381 - 393
  • [18] Synthesis and Biological Evaluation of 1α,25-Dihydroxyvitamin D3 Analogues Hydroxymethylated at C-26
    Regueira, Maria A.
    Samanta, Shaonly
    Malloy, Peter J.
    Ordonez-Moran, Paloma
    Resende, Diana
    Sussman, Fredy
    Munoz, Alberto
    Mourino, Antonio
    Feldman, David
    Torneiro, Mercedes
    JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (11) : 3950 - 3962
  • [19] Synthesis of spiro[4.5] decane CF-ring analogues of 1α,25-dihydroxyvitamin D3
    Schepens, Wim
    Van Haver, Dirk
    Vandewalle, Maurits
    Bouillon, Roger
    Verstuyf, Annemieke
    De Clercq, Pierre J.
    ORGANIC LETTERS, 2006, 8 (19) : 4247 - 4250
  • [20] Nonclassical effects of 1α,25-dihydroxyvitamin D3 and its analogs
    Verstuyf, A
    Verlinden, L
    Segaert, S
    Van Etten, E
    Mathieu, C
    Bouillon, R
    MINERAL AND ELECTROLYTE METABOLISM, 1999, 25 (4-6) : 345 - 348