A NOVEL SYNTHESIS OF AN A-RING PRECURSOR TO 1-ALPHA-HYDROXYVITAMIN-D

被引：28

作者：

DESCHRIJVER, J ^{[1
]}

DECLERCQ, PJ ^{[1
]}

机构：

[1] STATE UNIV GHENT,DEPT ORGAN CHEM,ORGAN SYNTH LAB,KRIJGSLAAN 281 S-4,B-9000 GHENT,BELGIUM

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 27期

关键词：

D O I：

10.1016/S0040-4039(00)79355-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel synthesis of the known, 1alpha-hydroxyvitamin D A-ring precursor 10, in racemic form, is described based upon (i) the stereoselective cycloaddition of allene-dienophile 2 onto 3-trimethylsilyloxyfuran 1 to give 3, and (ii) the samarium iodide induced reductive opening of the oxygen bridge in 4 to yield hydroxyketone 5, as key-steps.

引用

页码：4369 / 4372

页数：4

共 44 条

[1]

ANDREWS D, 1986, J ORG CHEM, V57, P1637

[2] 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

[3] 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

[4] SYNTHESIS OF TRIMETHYLSILYLOXY AND HYDROXY COMPOUNDS FROM CARBANIONS AND BIS(TRIMETHYLSILYL)PEROXIDE [J].

CAMICI, L ;

DEMBECH, P ;

RICCI, A ;

SECONI, G ;

TADDEI, M .

TETRAHEDRON, 1988, 44 (13) :4197-4206

[5] HETEROCYCLIC SILYL ENOL ETHER CHEMISTRY - SYNTHESIS AND REACTIVITY OF 3-TRIMETHYLSILOXYFURAN AND 3-TRIMETHYLSILOXYTHIOPHENE [J].

CAMICI, L ;

RICCI, A ;

TADDEI, M .

TETRAHEDRON LETTERS, 1986, 27 (42) :5155-5158

[6] AN ASYMMETRIC-SYNTHESIS OF A 1-ALPHA,25-DIHYDROXYVITAMIN-D3 A-RING SYNTHON [J].

CHEN, C ;

CRICH, D .

TETRAHEDRON LETTERS, 1992, 33 (15) :1945-1948

[7] STUDIES WITH TRIALKYLSILYLTRIFLATES - NEW SYNTHESES AND APPLICATIONS [J].

COREY, EJ ;

CHO, H ;

RUCKER, C ;

HUA, DH .

TETRAHEDRON LETTERS, 1981, 22 (36) :3455-3458

[8]

DELUCA H, COMPREHENSIVE MED CH, P1129

[9] ORGANOSELENIUM CHEMISTRY - FACILE ONE-STEP SYNTHESIS OF ALKYL ARYL SELENIDES FROM ALCOHOLS [J].

GRIECO, PA ;

GILMAN, S ;

NISHIZAWA, M .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (08) :1485-1486

[10] A NOVEL CONVERGENT SYNTHESIS OF (+)-1-ALPHA,25-DIHYDROXYVITAMIN-D3 USING A CHROMIUM(II)-MEDIATED COUPLING REACTION [J].

HATAKEYAMA, S ;

SUGAWARA, K ;

NUMATA, H ;

TAKANO, S .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (01) :461-463

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