HIGHLY DIASTEREOSELECTIVE BIS-HYDROXYLATION OF A PROTECTED CONDURITOL-B - A SHORT ROUTE TO MYOINOSITOL DERIVATIVES

被引：22

作者：

ARJONA, O

DEDIOS, A

DELAPRADILLA, RF ^{[1
]}

PLUMET, J

机构：

[1] CSIC,INST QUIM ORGAN,JUAN CIERVA 3,E-28006 MADRID,SPAIN

[2] UNIV COMPLUTENSE MADRID,FAC QUIM,DEPT QUIM ORGAN 1,E-28040 MADRID,SPAIN

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 49期

关键词：

GLYCOSYL-7-OXANORBORNANES; STEREOSELECTIVE REDUCTION; CONDURITOL-B; BIS-HYDROXYLATION; MYOINOSITOL DERIVATIVES;

D O I：

10.1016/0040-4039(91)80506-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Model studies on a synthesis of glycosylinositols via glycosyloxanorbornanes have resulted in a short and highly stereoselective synthesis of conveniently protected myo-inositols from 7-oxanorbornen-2-one featuring a highly diastereoselective catalytic osmylation of a protected Conduritol B.

引用

收藏

页码：7309 / 7312

页数：4

相关论文

共 44 条

[1] CHIRAL SYNTHESIS OF D-MYO-INOSITOL 1-PHOSPHATE STARTING FROM L-QUEBRACHITOL [J].

AKIYAMA, T ;

TAKECHI, N ;

OZAKI, S .

TETRAHEDRON LETTERS, 1990, 31 (10) :1433-1434

[2] POLAR VS STERIC EFFECTS IN THE 1,3-DIPOLAR CYCLOADDITION REACTIONS OF ACETONITRILE OXIDE AND 2-ENDO-ACETOXY-5-HALO-7-OXABICYCLO[2.2.1]HEPT-5-EN-2-EXO-CARBONITRILE [J].

ARJONA, O ;

DEDIOS, A ;

DELAPRADILLA, RF ;

MALLO, A ;

PLUMET, J .

TETRAHEDRON, 1990, 46 (24) :8179-8186

[3] REGIOSELECTIVE ELECTROPHILIC ADDITIONS TO 2-ALKOXY-7-OXABICYCLO[2.2.1]HEPT-5-ENE AND 2-ALKOXYMETHYL-7-OXABICYCLO[2.2.1]HEPT-5-ENE DERIVATIVES [J].

ARJONA, O ;

DELAPRADILLA, RF ;

PITAROMERO, I ;

PLUMET, J ;

VISO, A .

TETRAHEDRON, 1990, 46 (24) :8199-8206

[4] DESIGN AND SYNTHESIS OF 6-ALPHA-SUBSTITUTED 2-BETA,4-ALPHA-DIHYDROXY-1-BETA-PHOSPHORYLOXYCYCLOHEXANES, POTENT INHIBITORS OF INOSITOL MONOPHOSPHATASE [J].

BAKER, R ;

CARRICK, C ;

LEESON, PD ;

LENNON, IC ;

LIVERTON, NJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (05) :298-300

[5] GLYCOSYL-INOSITOL DERIVATIVES .3. SYNTHESIS OF HEXOSAMINE-INOSITOL-PHOSPHATES RELATED TO PUTATIVE INSULIN MEDIATORS [J].

BERLIN, WK ;

ZHANG, WS ;

SHEN, TY .

TETRAHEDRON, 1991, 47 (01) :1-20

[6]

BERRIDGE MJ, 1987, ANNU REV BIOCHEM, V56, P159, DOI 10.1146/annurev.bi.56.070187.001111

[7] RECENT DEVELOPMENTS IN THE SYNTHESIS OF MYOINOSITOL PHOSPHATES [J].

BILLINGTON, DC .

CHEMICAL SOCIETY REVIEWS, 1989, 18 (01) :83-122

[8] TOTAL SYNTHESIS OF MYOINOSITOL POLYPHOSPHATES FROM BENZENE VIA CONDURITOL-B DERIVATIVES [J].

CARLESS, HAJ ;

BUSIA, K .

TETRAHEDRON LETTERS, 1990, 31 (24) :3449-3452

[9] ON STEREOCHEMISTRY OF OSMIUM TETRAOXIDE OXIDATION OF ALLYLIC ALCOHOL SYSTEMS - EMPIRICAL RULE [J].

CHA, JK ;

CHRIST, WJ ;

KISHI, Y .

TETRAHEDRON, 1984, 40 (12) :2247-2255

[10] TOTAL SYNTHESIS OF HYGROMYCIN-A [J].

CHIDA, N ;

OHTSUKA, M ;

NAKAZAWA, K ;

OGAWA, S .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (07) :436-438

← 1 2 3 4 5 →