Novel synthetic approach to 19-nor-1α,25-dihydroxyvitamin D3 and its derivatives by Suzuki-Miyaura coupling in solution and on solid support

被引:40
作者
Hanazawa, T [1 ]
Wada, T [1 ]
Masuda, T [1 ]
Okamoto, S [1 ]
Sato, F [1 ]
机构
[1] Tokyo Inst Technol, Dept Biomol Engn, Midori Ku, Yokohama, Kanagawa 2268501, Japan
关键词
D O I
10.1021/ol016908r
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] 19-nor-1 alpha ,25-Dihydroxyvitamin D-3 was synthesized by the Suzuki-Miyaura coupling of the A-ring intermediate 3, which was efficiently prepared from readily available 5-(tert butyldimethylsilyl)oxycyclohex-2-enone (5), with the boronate compound of the C,D-ring portion. The method could be applied to a solid-phase synthesis to prepare the des-C,D derivatives of 19-nor-1 alpha ,25-dihydroxyvitamin D-3.
引用
收藏
页码:3975 / 3977
页数:3
相关论文
共 33 条
[11]  
Hareau-Vittini G, 1998, ANGEW CHEM INT EDIT, V37, P2099, DOI 10.1002/(SICI)1521-3773(19980817)37:15<2099::AID-ANIE2099>3.0.CO
[12]  
2-U
[13]   Parallel synthesis of a vitamin D3 library in the solid-phase [J].
Hijikuro, I ;
Doi, T ;
Takahashi, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (16) :3716-3722
[14]   Efficient and practical synthesis of optically active 5-t-butyldimethylsiloxy-2-cyclohexenone as a convenient chiral 2,5-cyclohexadienone synthon [J].
Hikichi, S ;
Hareau, GPJ ;
Sato, F .
TETRAHEDRON LETTERS, 1997, 38 (48) :8299-8302
[15]   Novel versatile approach to an enantiopure 19-nor, des-C,D vitamin D3 derivative [J].
Hilpert, H ;
Wirz, B .
TETRAHEDRON, 2001, 57 (04) :681-694
[16]   Novel polymer-supported trialkylsilanes and their use in solid-phase organic synthesis [J].
Hu, YH ;
Porco, JA ;
Labadie, JW ;
Gooding, OW ;
Trost, BM .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (13) :4518-4521
[17]   An efficient enantioselective synthesis of 1α,25-dihydroxyvitamin D3 A-ring synthon [J].
Koiwa, M ;
Hareau, GPJ ;
Sato, F .
TETRAHEDRON LETTERS, 2000, 41 (14) :2389-2390
[18]   Biological activities of 19-nor-1α,25-dihydroxyvitamin D3 analogs singly dehydroxylated at the C-1 or C-3 position of the A-ring [J].
Kubodera, N ;
Okano, T ;
Nakagawa, K ;
Ozono, K ;
Mikami, K .
CURRENT PHARMACEUTICAL DESIGN, 2000, 6 (07) :791-801
[19]   Symmetry in the synthesis of the A-ring of a vitamin D hybrid analogue with significant transactivation activity: A combinatorial sequence of regioselective propiolate-ene, catalytic enantioselective epoxidation and carbonyl-ene cyclization reactions [J].
Mikami, K ;
Osawa, A ;
Isaka, A ;
Sawa, E ;
Shimizu, M ;
Terada, M ;
Kubodera, N ;
Nakagawa, K ;
Tsugawa, N ;
Okano, T .
TETRAHEDRON LETTERS, 1998, 39 (21) :3359-3362
[20]   PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF ORGANOBORON COMPOUNDS [J].
MIYAURA, N ;
SUZUKI, A .
CHEMICAL REVIEWS, 1995, 95 (07) :2457-2483