ASYMMETRIC-SYNTHESIS OF A KEY 1-ALPHA,25-DIHYDROXY-VITAMIN-D3 RING-A SYNTHON

被引:34
作者
KABAT, MM
LANGE, M
WOVKULICH, PM
USKOKOVIC, MR
机构
[1] Roche Research Center, Hoffmann-La Roche Inc., Nutley
关键词
D O I
10.1016/0040-4039(93)88021-A
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient and highly stereoselective synthesis of the A-ring synthon 4 of 1,25(OH)2-vitamin D3 (1) is described. The aldehyde 12, which was used for an intramolecular ene reaction to form the main framework 18, was obtained by two different asymmetric approaches starting from olefin 6.
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收藏
页码:7701 / 7704
页数:4
相关论文
共 18 条
[1]   STEREOSELECTIVE TOTAL SYNTHESIS OF "1-ALPHA,25-DIHYDROXYCHOLECALCIFEROL [J].
BAGGIOLINI, EG ;
IACOBELLI, JA ;
HENNESSY, BM ;
USKOKOVIC, MR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (10) :2945-2948
[2]   STEREOCONTROLLED TOTAL SYNTHESIS OF "1-ALPHA,25-DIHYDROXYCHOLECALCIFEROL AND 1-ALPHA,25-DIHYDROXYERGOCALCIFEROL [J].
BAGGIOLINI, EG ;
IACOBELLI, JA ;
HENNESSY, BM ;
BATCHO, AD ;
SERENO, JF ;
USKOKOVIC, MR .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (16) :3098-3108
[3]   AN APPROACH TO THE SYNTHESIS OF THE HEXAHYDRONAPHTHALENE UNIT OF PRAVASTATIN [J].
BARRISH, JC ;
WOVKULICH, PM ;
TANG, PC ;
BATCHO, AD ;
USKOKOVIC, MR .
TETRAHEDRON LETTERS, 1990, 31 (16) :2235-2238
[4]   NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS [J].
DALE, JA ;
MOSHER, HS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :512-519
[5]  
DANIEWSKI AR, 1992, J ORG CHEM, V57
[6]  
DEGRUYTER W, 1991, 8TH P WORKSH VIT D
[7]   REDUCTIVE RING OPENINGS OF ALLYL-ALCOHOL EPOXIDES [J].
FINAN, JM ;
KISHI, Y .
TETRAHEDRON LETTERS, 1982, 23 (27) :2719-2722
[8]   CATALYTIC ASYMMETRIC EPOXIDATION AND KINETIC RESOLUTION - MODIFIED PROCEDURES INCLUDING INSITU DERIVATIZATION [J].
GAO, Y ;
HANSON, RM ;
KLUNDER, JM ;
KO, SY ;
MASAMUNE, H ;
SHARPLESS, KB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (19) :5765-5780
[9]   THE 1ST PRACTICAL METHOD FOR ASYMMETRIC EPOXIDATION [J].
KATSUKI, T ;
SHARPLESS, KB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (18) :5974-5976
[10]  
KIEGIEL J, 1991, TETRAHEDRON LETT, V32, P6057, DOI 10.1016/0040-4039(91)80752-R