Radical cyclization in heterocycle synthesis. Part 9: A novel synthesis of aminocyclitols and related compounds via stannyl radical cyclization of oxime ethers derived from sugars

被引：36

作者：

Kiguchi, T ^{[1
]}

Tajiri, K ^{[1
]}

Ninomiya, I ^{[1
]}

Naito, T ^{[1
]}

机构：

[1] Kobe Pharmaceut Univ, Kobe, Hyogo 6588558, Japan

来源：

TETRAHEDRON | 2000年 / 56卷 / 32期

关键词：

amino alcohols; piperidines; radicals and radical reactions; ring transformations;

D O I：

10.1016/S0040-4020(00)00545-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Stannyl radical addition-cyclization of oxime ethers derived from D-glucose, D-galactose, and D-xylose proceeded smoothly to afford alkoxyamino alcohols which were effectively converted into two types of glycosidase inhibitors or its candidates such as aminocyclitols, 1-deoxynojirimycin, and 1-deoxygalactostatin via reductive ring-expansion of trans alkoxyamino alcohols. (C) 2000 Elsevier Science Ltd. All rights reserved.

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页码：5819 / 5833

页数：15

相关论文

共 22 条

[1] 2,3,46-TETRA-O-BENZYL-D-GALACTOSYL CHLORIDE AND ITS USE IN SYNTHESIS OF ALPHA- AND BETA-D-GALACTOPYRANOSIDES [J].

AUSTIN, PW ;

HARDY, FE ;

BUCHANAN, JG ;

BADDILEY, J .

JOURNAL OF THE CHEMICAL SOCIETY, 1965, (FEB) :1419-&

[2] RADICAL CYCLIZATION OF OXIME ETHERS [J].

BARTLETT, PA ;

MCLAREN, KL ;

TING, PC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (05) :1633-1634

[3] Synthesis and biological activity of natural aminocyclopentitol glycosidase inhibitors: Mannostatins, trehazolin, allosamidins, and their analogues [J].

Berecibar, A ;

Grandjean, C ;

Siriwardena, A .

CHEMICAL REVIEWS, 1999, 99 (03) :779-844

[4] 1-aza sugars, apparent transition state analogues of equatorial glycoside formation/cleavage [J].

Bols, M .

ACCOUNTS OF CHEMICAL RESEARCH, 1998, 31 (01) :1-8

[5] A NOVEL RING EXPANSION REACTION IN THE REDUCTION OF BENZYLIC METHOXYAMINES WITH LITHIUM ALUMINUM-HYDRIDE [J].

BOOTH, SE ;

JENKINS, PR ;

SWAIN, CJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (02) :147-148

[6] Synthesis and evaluation of aminocyclopentitol inhibitors of β-glucosidases [J].

Boss, O ;

Leroy, E ;

Blaser, A ;

Reymond, JL .

ORGANIC LETTERS, 2000, 2 (02) :151-154

[7]

CHEN S, 1974, SYNTHESIS-STUTTGART, P691

[8] INTRAMOLECULAR REDUCTIVE COUPLING OF CARBONYL-TETHERED OXIME ETHERS PROMOTED BY SAMARIUM DIIODIDE - A POWERFUL METHOD FOR THE STEREOSELECTIVE SYNTHESIS OF AMINOCYCLOPENTITOLS [J].

CHIARA, JL ;

MARCOCONTELLES, J ;

KHIAR, N ;

GALLEGO, P ;

DESTABEL, C ;

BERNABE, M .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (19) :6010-6011

[9] SYNTHESIS OF A GLUCOSE-DERIVED TETRAZOLE AS A NEW BETA-GLUCOSIDASE INHIBITOR - A NEW SYNTHESIS OF 1-DEOXYNOJIRIMYCIN [J].

ERMERT, P ;

VASELLA, A .

HELVETICA CHIMICA ACTA, 1991, 74 (08) :2043-2053

[10] Anomer-selective inhibition of glycosidases using aminocyclopentanols [J].

Leroy, E ;

Raymond, JL .

ORGANIC LETTERS, 1999, 1 (05) :775-777