Efficient and practical synthesis of the A-ring precursor of 19-nor-1α,25-dihydroxyvitamin D3 and its 13C, or 2H-labeled derivative

被引:18
作者
Hanazawa, T [1 ]
Inamori, H [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/ol016052q
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] The A-ring precursor of 19-nor-1 alpha ,25-dihydroxyvitamin D-3 (1) and its C-13- or H-2-labeled derivative were efficiently synthesized from readily available, optically active 5-(tert-butyldimethylsilyloxy)-2-cyclohexenone (2) through a five step reaction in 68% overall yield.
引用
收藏
页码:2205 / 2207
页数:3
相关论文
共 23 条
[1]   Asymmetric synthesis of a key ring a synthon for 1α-hydroxy-19-norvitamin D [J].
Courtney, LF ;
Lange, M ;
Uskokovic, MR ;
Wovkulich, PM .
TETRAHEDRON LETTERS, 1998, 39 (21) :3363-3366
[2]  
FELDMAN D, 1995, VITAMIN D, V16, P200
[3]  
Graul A., 1998, Drugs of the Future, V23, P602, DOI 10.1358/dof.1998.023.06.461708
[4]  
HANAZAWA T, IN PRESS TETRAHEDRON
[5]   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
[6]   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
[7]   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
[8]  
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
[9]  
2-U
[10]   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