SYNTHESIS OF (C-11)-SUBSTITUTED ANALOGS OF 1-ALPHA,25-DIHYDROXYVITAMIN-D3

被引：11

作者：

DHALLEWEYN, C ^{[1
]}

VANHAVER, D ^{[1
]}

VANDEREYCKEN, J ^{[1
]}

DECLERCQ, P ^{[1
]}

VANDEWALLE, M ^{[1
]}

机构：

[1] STATE UNIV GHENT,ORGAN SYNTH LAB,KRIJGSLAAN 281 S4,B-9000 GHENT,BELGIUM

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1992年 / 2卷 / 05期

关键词：

D O I：

10.1016/S0960-894X(00)80173-0

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The synthesis of a series of C-ring modified analogues of 1-alpha,25-dihydroxyvitamin D3, with various alpha- and beta-oriented substituents on C-11, is described. It includes the construction of the 25-hydroxylated side-chain, the stereoselective introduction of the substituents at C-11 via conjugate organocuprate addition, and coupling with the A-ring.

引用

页码：477 / 480

页数：4

共 17 条

[1] 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

[2] EFFECTS OF A NOVEL VITAMIN-D ANALOG MC-903 ON CELL-PROLIFERATION AND DIFFERENTIATION INVITRO AND ON CALCIUM-METABOLISM INVIVO [J].

BINDERUP, L ;

BRAMM, E .

BIOCHEMICAL PHARMACOLOGY, 1988, 37 (05) :889-895

[3]

BOUILLON R, 1989, SAUDI MED J, V10, P260

[4]

BOUILLON R, Patent No. 341158

[5]

BOUILLON R, IN PRESS J BIOL CHEM

[6] ANHYDROUS TETRABUTYLAMMONIUM FLUORIDE - A MILD BUT HIGHLY EFFICIENT SOURCE OF NUCLEOPHILIC FLUORIDE-ION [J].

COX, DP ;

TERPINSKI, J ;

LAWRYNOWICZ, W .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (17) :3216-3219

[7] VITAMIN-D AND THE KIDNEY [J].

HOLICK, MF .

KIDNEY INTERNATIONAL, 1987, 32 (06) :912-929

[8] STRUCTURES AND BIOLOGICAL-ACTIVITIES OF VITAMIN-D METABOLITES AND THEIR ANALOGS [J].

IKEKAWA, N .

MEDICINAL RESEARCH REVIEWS, 1987, 7 (03) :333-366

[9] THE CHEMISTRY OF HIGHER-ORDER ORGANOCUPRATES [J].

LIPSHUTZ, BH ;

WILHELM, RS ;

KOZLOWSKI, JA .

TETRAHEDRON, 1984, 40 (24) :5005-5038

[10]

LIPSHUTZ BH, 1987, SYNTHESIS-STUTTGART, P325

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