Catalytic Ferrier rearrangement of unsaturated nucleosides

被引：12

作者：

Linker, T

Sommermann, T

Gimisis, T

Chatgilialoglu, C

机构：

[1] Univ Stuttgart, Inst Organ Chem, D-70569 Stuttgart, Germany

[2] CNR, ICoCEA, I-40129 Bologna, Italy

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 52期

关键词：

nucleosides; radical reactions; rearrangements;

D O I：

10.1016/S0040-4039(98)02264-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The attempted intermolecular addition of malonyl radicals to 1',2'-unsaturated nucleosides has led to the unexpected formation of furanones. Thus, only catalytic amounts of ceric(IV) ammonium nitrate (CAN), induce a Ferrier rearrangement. The unsaturated lactone was isolated in good yield and can serve as a precursor for the synthesis of optically active products. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：9637 / 9638

页数：2

相关论文

共 14 条

[1] An unexpected photoadduct of N-carbomethoxymethylpyrrolidine with a chiral butenolide and benzophenone: X-ray structure and synthetic utility [J].

deAlvarenga, ES ;

Cardin, CJ ;

Mann, J .

TETRAHEDRON, 1997, 53 (04) :1457-1466

[2] UNSATURATED CARBOHYDRATES .11. ISOMERISATION AND DIMERISATION OF TRI-O-ACETYL-D-GLUCAL [J].

FERRIER, RJ ;

PRASAD, N .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1969, (04) :581-&

[3] SOME PROGENY OF 2,3-UNSATURATED SUGARS - THEY LITTLE RESEMBLE GRANDFATHER GLUCOSE - 10 YEARS LATER [J].

FRASERREID, B .

ACCOUNTS OF CHEMICAL RESEARCH, 1985, 18 (11) :347-354

[4] Generation of C-1′ radicals through a β-(acyloxy)alkyl rearrangement in modified purine and pyrimidine nucleosides [J].

Gimisis, T ;

Ialongo, G ;

Chatgilialoglu, C .

TETRAHEDRON, 1998, 54 (3-4) :573-592

[5]

HAFELE B, 1987, LIEBIGS ANN CHEM, P85

[6]

INABA VK, 1991, CHEM LETT, P485

[7] REACTIONS OF 2'-DEOXY-2'-HALOURIDINES AND O(2),2'-CYCLOURIDINE WITH LITHIUM DIALKYLAMIDES - FORMATION OF 1',2'-UNSATURATED DERIVATIVES [J].

KITTAKA, A ;

TANAKA, H ;

MIYASAKA, T ;

YAMAGUCHI, K .

NUCLEOSIDES & NUCLEOTIDES, 1992, 11 (01) :37-47

[8] NEW MECHANISTIC PROPOSAL FOR SOME HEPTAMOLYBDATE-ION-CATALYZED ISOMERIZATIONS [J].

KLAIC, B ;

RAZA, Z ;

SANKOVIC, M ;

SUNJIC, V .

HELVETICA CHIMICA ACTA, 1987, 70 (01) :59-62

[9] Transition-metal-mediated radical reactions. 3. Transition-metal-mediated radical reactions as an easy route to 2-C-analogues of carbohydrates [J].

Linker, T ;

Hartmann, K ;

Sommermann, T ;

Scheutzow, D ;

Ruckdeschel, E .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (15) :1730-1732

[10] The addition of malonates to glycals: A general and convenient method for the synthesis of 2-C-branched carbohydrates [J].

Linker, T ;

Sommermann, T ;

Kahlenberg, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (40) :9377-9384