FURANOSIDES AND FURANONES BEARING ACRYLATE SIDE-CHAINS VIA PALLADIUM-MEDIATED CYCLIZATIONS OF GAMMA-OXOALLENES

被引：31

作者：

WALKUP, RD

MOSHER, MD

机构：

[1] Department of Chemistry and Biochemistry, Texas Tech University, Lubbock

来源：

TETRAHEDRON | 1993年 / 49卷 / 41期

关键词：

D O I：

10.1016/0040-4020(93)80015-L

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of 4,5-hexadienal with catalytic palladium(II) chloride and excess copper(II) chloride, methanol and carbon monoxide in the presence of an acid and a water scavenger resulted in a net acetalization-cyclization-methoxycarbonylation to form a novel methyl furanoside bearing a methyl acrylate sidechain. Treatment of 4,5-hexadienoic acid under the same conditions yields the corresponding furanone, and 3-(tert-butylidimethylsilyloxy)-4,5-hexadienal yields a methyl beta-3'-(tert-butyldimethylsilyloxy)-2'-deoxyribofuranoside bearing the acrylate sidechain, with high stereoselectivity. This methodology provides access to sidechain-branched ribofuranoside compounds.

引用

收藏

页码：9285 / 9294

页数：10

相关论文

共 21 条

[1]

ARSINIYADIS S, 1979, TETRAHEDRON, V35, P353

[2] ANNELATIVE RING EXPANSION VIA INTRAMOLECULAR [2 + 2] PHOTOCYCLOADDITION OF ALPHA,BETA-UNSATURATED GAMMA-LACTONES AND REDUCTIVE CLEAVAGE - SYNTHESIS OF HYDROCYCLOPENTACYCLOOCTENE-5-CARBOXYLATES [J].

COATES, RM ;

SENTER, PD ;

BAKER, WR .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (19) :3597-3607

[3] ALLENES .24. PREPARATION OF ALPHA-ALLENIC ALCOHOLS FROM MONO-O-TETRAHYDROPYRAN-2-YL DERIVATIVES OF BUTYNE-1,4-DIOLS [J].

COWIE, JS ;

LANDOR, PD ;

LANDOR, SR .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (07) :720-724

[4]

CRABBE P, 1984, ORG SYN, V63, P203

[5] SYNTHESIS OF 5'-C-CHAIN-EXTENDED URIDINES BY REACTION OF 5'-HALONUCLEOSIDES WITH MALONIC-ACID TYPE DERIVATIVES [J].

FIANDOR, J ;

GARCIALOPEZ, MT ;

DELASHERAS, FG .

NUCLEOSIDES & NUCLEOTIDES, 1989, 8 (07) :1325-1334

[6] IODOCYCLIZATION OF THE (TOLYLSULFONYL)CARBAMATES AND (TRICHLOROACETYL)CARBAMATES OF SECONDARY ALPHA-ALLENIC ALCOHOLS - HIGHLY DIASTEREOSELECTIVE SYNTHESIS OF SYN-1,2-AMINO ALCOHOLS AND TRANS-5-ALKYL-2-OXO-OXAZOLIDINE-4-CARBOXYLIC ACIDS [J].

FRIESEN, RW ;

KOLACZEWSKA, AE .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (16) :4888-4895

[7] ELECTROPHILE-MEDIATED CYCLIZATIONS INVOLVING THE ALLENE PI-SYSTEM - STEREOSELECTIVITY AND SYNTHETIC UTILITY OF PD(II)-CATALYZED HETEROATOM CYCLIZATION REACTIONS - X-RAY MOLECULAR-STRUCTURE OF METHYL 2-[TRANS-3-PHENYL-N-(PARA-TOLYLSULFONYL)PYRROLIDIN-2-YL]ACRYLATE [J].

GALLAGHER, T ;

DAVIES, IW ;

JONES, SW ;

LATHBURY, D ;

MAHON, MF ;

MOLLOY, KC ;

SHAW, RW ;

VERNON, P .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (04) :433-440

[8] 1-(3'-AZIDO-2',3',5'-TRIDEOXY-BETA-D-ALLOFURANOSYL) THYMINE - A SIDE-CHAIN HOMOLOG OF 3'-AZIDO-3'-DEOXYTHYMIDINE [J].

HIEBL, J ;

ZBIRAL, E .

TETRAHEDRON LETTERS, 1990, 31 (28) :4007-4010

[9] SYNTHESIS OF 1-DEUTERIATED AND 1,2,2'-DEUTERIATED DEOXYRIBOSE AND INCORPORATION INTO DEOXYRIBONUCLEOSIDES [J].

HODGE, RP ;

BRUSH, CK ;

HARRIS, CM ;

HARRIS, TM .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (04) :1553-1564

[10] CONVERSION OF 2',3'-O-ISOPROPYLIDENEADENOSINE INTO 9-(6-DEOXY-BETA-D-ALLOFURANOSYL)-AND 9-(6-DEOXY-ALPHA-L-TALOFURANOSYL)-ADENINES [J].

HOWGATE, P ;

HAMPTON, A .

CARBOHYDRATE RESEARCH, 1972, 21 (02) :309-&