Novel synthetic approach to 1 alpha,24(R)-dihydroxyvitamin D-3 using an asymmetric nitroaldol reaction

被引:24
作者
Oshida, J [1 ]
Okamoto, M [1 ]
Azuma, S [1 ]
Tanaka, T [1 ]
机构
[1] TEIJIN LTD,IWAKUNI PHARMACEUT FACTORY,CHEM MFG PLANT,YAMAGUCHI 740,JAPAN
关键词
D O I
10.1016/S0957-4166(97)00312-1
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Rare earth-K-(S)-BINOL complexes were used to catalyze the nitroaldol reaction of the CD-ring 24-aldehyde precursors with 2-nitropropane in a good stereoselective manner. The obtained nitroaldol compound was easily converted into a synthetic intermediate 12 of 1 alpha,24(R)-dihydroxyvitamin D-3 1 by a denitration reaction using 2,2'-azobisisobutyronitrile (AIBN) and Bu3SnH. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:2579 / 2584
页数:6
相关论文
共 26 条
[1]  
BARLAAM B, 1995, TETRAHEDRON, V51, P1684
[2]   APPROACHES TO CARBOCYCLIC ANALOGS OF THE POTENT NEURAMINIDASE INHIBITOR 4-GUANIDINO-NEU5AC2EN - X-RAY MOLECULAR-STRUCTURE OF N-[(1S,2S,6R)-2-AZIDO-6-BENZYLOXYMETHYL-4-FORMYLCYCLOHEX-3-ENYL]ACETAMIDE [J].
CHANDLER, M ;
CONROY, R ;
COOPER, AWJ ;
LAMONT, RB ;
SCICINSKI, JJ ;
SMART, JE ;
STORER, R ;
WEIR, NG ;
WILSON, RD ;
WYATT, PG .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (09) :1189-1197
[3]   HIGHLY EFFICIENT NITROALDOL REACTION PROMOTED BY TRIALKYLSILYL CHLORIDES [J].
FERNANDEZ, R ;
GASCH, C ;
GOMEZSANCHEZ, A ;
VILCHEZ, JE .
TETRAHEDRON LETTERS, 1991, 32 (27) :3225-3228
[4]  
KOBAYASHI T, 1990, Journal of Dermatology (Tokyo), V17, P707
[5]   SYNTHESIS OF SPHINGANINE ANALOGS MODIFIED IN THE HEAD GROUP [J].
KOLTER, T ;
VANECHTENDECKERT, G ;
SANDHOFF, K .
TETRAHEDRON, 1994, 50 (47) :13425-13432
[6]   ASYMMETRIC REDUCTIONS .7. THE ACTION OF THE GRIGNARD REAGENT FROM (+)-1-CHLORO-2-METHYLBUTANE ON A SERIES OF ALKYL PHENYL KETONES [J].
MACLEOD, R ;
WELCH, FJ ;
MOSHER, HS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (04) :876-880
[7]   SYNTHESIS AND CONFORMATIONAL STUDIES OF BETA-(1-]6)-LINKED AND BETA,BETA-(1-]1)-LINKED C-DISACCHARIDES [J].
MARTIN, OR ;
LAI, W .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (01) :176-185
[8]  
MATSUMOTO K, 1990, Journal of Dermatology (Tokyo), V17, P97
[9]  
MATSUNAGA T, 1990, Journal of Dermatology (Tokyo), V17, P135
[10]   SYNTHESIS OF ACTIVE FORMS OF VITAMIN-D .9. SYNTHESIS OF "1-ALPHA,24-DIHYDROXYCHOLECALCIFEROL [J].
MORISAKI, M ;
KOIZUMI, N ;
IKEKAWA, N ;
TAKESHITA, T ;
ISHIMOTO, S .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (14) :1421-1424