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
[1]   STRUCTURE-FUNCTION-RELATIONSHIPS IN THE VITAMIN-D ENDOCRINE SYSTEM [J].
BOUILLON, R ;
OKAMURA, WH ;
NORMAN, AW .
ENDOCRINE REVIEWS, 1995, 16 (02) :200-257
[2]  
DAI HY, 1994, SYNTHESIS-STUTTGART, P1383
[3]   An efficient solid-phase synthesis of the vitamin D3 system [J].
Doi, T ;
Hijikuro, I ;
Takahashi, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (28) :6749-6750
[4]  
Feldman D., 1997, VITAMIN D
[5]  
Graul A., 1998, Drugs of the Future, V23, P602, DOI 10.1358/dof.1998.023.06.461708
[6]   Chemical synthesis of optically active cis-cyclohexa-3,5-diene-1,2-diols and their 5-2H-derivatives [J].
Hanazawa, T ;
Okamoto, S ;
Sato, F .
TETRAHEDRON LETTERS, 2001, 42 (32) :5455-5457
[7]   Efficient and practical synthesis of the A-ring precursor of 19-nor-1α,25-dihydroxyvitamin D3 and its 13C, or 2H-labeled derivative [J].
Hanazawa, T ;
Inamori, H ;
Masuda, T ;
Okamoto, S ;
Sato, F .
ORGANIC LETTERS, 2001, 3 (14) :2205-2207
[8]   Asymmetric synthesis of palitantin from the (5R)-tert-butyldimethylsiloxy-2-cyclohexenone [J].
Hareau, G ;
Koiwa, M ;
Hanazawa, T ;
Sato, F .
TETRAHEDRON LETTERS, 1999, 40 (42) :7493-7496
[9]   Asymmetric synthesis of 1α,25-dihydroxyvitamin D3 A-ring precursor starting with 5-tert-butyldimethylsiloxy-2-cyclohexenone [J].
Hareau, GPJ ;
Koiwa, M ;
Sato, F .
TETRAHEDRON LETTERS, 2000, 41 (14) :2385-2388
[10]   Synthesis of optically active 5-(tert-butyldimethylsiloxy)-2-cyclohexenone and its 6-substituted derivatives as useful chiral building blocks for the synthesis of cyclohexane rings.: Syntheses of carvone, penienone, and penihydrone [J].
Hareau, GPJ ;
Koiwa, M ;
Hikichi, S ;
Sato, F .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (15) :3640-3650