Simple, efficient chemoenzymatic synthesis of (S)-5-(tert-butyldimethylsilyloxy)-2-cyclohexenone and enantiomeric ketone intermediates of 19-Nor-1α,25-dihydroxyvitamin D3

被引:14
作者
Kalkote, UR [1 ]
Ghorpade, SR [1 ]
Chavan, SP [1 ]
Ravindranathan, T [1 ]
机构
[1] Natl Chem Lab, Div Organ Chem Technol, Pune 411008, Maharashtra, India
关键词
D O I
10.1021/jo016141g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[No abstract available]
引用
收藏
页码:8277 / 8281
页数:5
相关论文
共 21 条
[1]  
BJORKLING F, 1985, TETRAHEDRON LETT, V26, P4975
[2]  
BOUILLON R, 1993, J BONE MINER RES, V8, P1009
[3]  
FROASH JV, 1974, J CHEM SOC P1, P2005
[4]   Efficient synthesis of optically pure (4R,6S)-4-(tert-butyldimethylsilyloxy)-6-(hydroxymethyl)tetrahydropyran-2-one and its enantiomer [J].
Ghorpade, SR ;
Kalkote, UR ;
Chavan, SP ;
Bhide, SR ;
Ravindranathan, T ;
Puranik, VG .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (20) :6803-6806
[5]  
HAMDA K, 1993, DRUGS FUTURE, V16, P1057
[6]   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
[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]   A NOVEL SYNTHESIS OF 19-NOR 1-ALPHA,25-DIHYDROXYVITAMIN D-3 AND RELATED ANALOGS [J].
HUANG, PQ ;
SABBE, K ;
POTTIE, M ;
VANDEWALLE, M .
TETRAHEDRON LETTERS, 1995, 36 (45) :8299-8302
[9]   SELECTIVE REMOVAL OF TETRAHYDROPYRANYL ETHERS IN THE PRESENCE OF TERT-BUTYLDIMETHYLSILYL ETHERS WITH MAGNESIUM BROMIDE IN ETHER [J].
KIM, S ;
PARK, JH .
TETRAHEDRON LETTERS, 1987, 28 (04) :439-440
[10]   CALCIFEROL AND ITS RELATIVES .22. DIRECT TOTAL SYNTHESIS OF VITAMIN-D2 AND VITAMIN-D3 [J].
LYTHGOE, B ;
MORAN, TA ;
NAMBUDIRY, MEN ;
TIDESWELL, J ;
WRIGHT, PW .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1978, (06) :590-595