Improved preparation of A-ring phosphine oxides for the synthesis of vitamin D analogs

被引:5
作者
Daniewski, AR [1 ]
Garofalo, LN [1 ]
Kabat, MM [1 ]
机构
[1] Hoffmann La Roche Inc, Preclin Res & Dev, Nonclin Dev, Chem Synth Proc Res, Nutley, NJ 07110 USA
关键词
D O I
10.1081/SCC-120012994
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new, high yielding, two-step process for the preparation of A-ring phospine oxides from allyl alcohols, useful for the synthesis of vitamin D analog, is described, in which triphosgene and diphenylphosphine oxide arc used for chlorination and subsequent substitution reactions, respectively.
引用
收藏
页码:3031 / 3039
页数:9
相关论文
共 17 条
[1]  
Anné S, 1999, SYNLETT, P1435
[2]  
BAGILLINI EG, 1986, J ORG CHEM, V51, P3098
[3]  
BAGIOLLINI EG, 1982, J AM CHEM SOC, V104, P2945
[4]   Efficient fluorination with tetrabutylammonium dihydrogen trifluoride in a novel approach toward 1-α-fluoro-25-hydroxy-vitamin D3 analogues [J].
Barbier, P ;
Mohr, P ;
Muller, M ;
Masciadri, R .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (20) :6984-6989
[5]  
BOULLION R, 1995, ENDOCR REV, V16, P200
[6]  
COREY EJ, 1972, TETRAHEDRON LETT, P4339
[7]   Comment on "Chemical safety. Safe handing of triphosgene [bis(trichloromethyl)carbonate]" [J].
Cotarca, L .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 1999, 3 (05) :377-377
[8]  
DAI HY, 1994, SYNTHESIS-STUTTGART, P1383
[9]   FACILE CHLORIDE SUBSTITUTION OF ACTIVATED ALCOHOLS BY TRIPHOSGENE - APPLICATION TO CEPHALOSPORIN CHEMISTRY [J].
GOREN, Z ;
HEEG, MJ ;
MOBASHERY, S .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (25) :7186-7188
[10]   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