Stereoselective synthesis of vitamin D3 analogues with cyclic side chains

被引：10

作者：

Fall, Y ^{[1
]}

Fernandez, C

Vitale, C

Mouriño, A

机构：

[1] Univ Vigo, Fac Ciencias, Dept Quim Fis & Quim Organ, Vigo 36200, Spain

[2] Univ Santiago de Compostela, CSIC, Dept Quim Organ, Santiago De Compostela 15706, Spain

[3] Univ Santiago de Compostela, CSIC, Unidad Asociada, Santiago De Compostela 15706, Spain

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 38期

关键词：

D O I：

10.1016/S0040-4039(00)01220-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of a new class of vitamin D analogues having a cyclic side chain is described. Readily available starting material, a short sequence with high yielding steps are key features of the synthesis. Alcohols 12c and 12d were readily separable by flash chromatography and the stereochemistry at C22 was established unambiguously by X-ray diffraction analysis of 12c. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：7323 / 7326

页数：4

共 13 条

[1] SYNTHESIS OF 25-HYDROXY-VITAMIN-D3 AND 1-ALPHA,25-DIHYDROXYVITAMIN-D3 FROM VITAMIN-D2 (CALCIFEROL) [J].

ANDREWS, DR ;

BARTON, DHR ;

HESSE, RH ;

PECHET, MM .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (25) :4819-4828

[2] STRUCTURE-FUNCTION-RELATIONSHIPS IN THE VITAMIN-D ENDOCRINE SYSTEM [J].

BOUILLON, R ;

OKAMURA, WH ;

NORMAN, AW .

ENDOCRINE REVIEWS, 1995, 16 (02) :200-257

[3]

DELUCA HF, 1990, KIDNEY INT S S, V29, P2

[4] An efficient stereoselective synthesis of 1 alpha,24(R)-dihydroxyvitamin D-3 by the dienyne route. [J].

Fall, Y ;

Torneiro, M ;

Castedo, L ;

Mourino, A .

TETRAHEDRON, 1997, 53 (13) :4703-4714

[5]

Feldman D., 1997, VITAMIN D

[6] STUDIES ON VITAMIN-D (CALCIFEROL) AND ITS ANALOGS .23. EFFECT OF 3-METHYL SUBSTITUENTS ON THE THERMAL [1,5]-SIGMATROPIC AND [1,7]-SIGMATROPIC HYDROGEN SHIFTS OF VINYLALLENES AND OTHER SECO STEROIDS RELATED TO VITAMIN-D - SYNTHESIS OF 3-METHYL-SUBSTITUTED AND 3,3-DIMETHYL-SUBSTITUTED ANALOGS OF 3-DEOXY-1-ALPHA,25-DIHYDROXYVITAMIN-D3IN [J].

LEYES, GA ;

OKAMURA, WH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (22) :6099-6105

[7] 1,25(OH)2-VITAMIN-D3 RECEPTORS - GENE-REGULATION AND GENETIC CIRCUITRY [J].

MINGHETTI, PP ;

NORMAN, AW .

FASEB JOURNAL, 1988, 2 (15) :3043-3053

[8] Efficient and versatile synthesis of A-ring precursors of 1 alpha,25-dihydroxy-vitamin D-3 and analogues. Application to the synthesis of Lythgoe-Roche phosphine oxide. [J].

Mourino, A ;

Torneiro, M ;

Vitale, C ;

Fernandez, S ;

PerezSestelo, J ;

Anne, S ;

Gregorio, C .

TETRAHEDRON LETTERS, 1997, 38 (26) :4713-4716

[9] THE ROLE OF THE VITAMIN-D ENDOCRINE SYSTEM IN HEALTH AND DISEASE [J].

REICHEL, H ;

KOEFFLER, HP ;

NORMAN, AW .

NEW ENGLAND JOURNAL OF MEDICINE, 1989, 320 (15) :980-991

[10] STUDIES ON THE SYNTHESIS OF SIDE-CHAIN HYDROXYLATED METABOLITES OF VITAMIN-D .2. STEREOCONTROLLED SYNTHESIS OF 25-HYDROXYVITAMIN-D2 [J].

SARDINA, FJ ;

MOURINO, A ;

CASTEDO, L .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (08) :1264-1269

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