Zinc(II) triflate-controlled 1,3-dipolar cycloadditions of C-(2-thiazolyl)nitrones: Application to the synthesis of a novel isoxazolidinyl analogue of tiazofurin

被引：44

作者：

Chiacchio, U

Rescifina, A

Saita, MG

Iannazzo, D

Romeo, G

Mates, JA

Tejero, T

Merino, P

机构：

[1] Univ Catania, Dipartimento Sci Chim, I-95125 Catania, Italy

[2] Univ Messina, Dipartimento Farmacochim, I-98168 Messina, Italy

[3] Univ Zaragoza, ICMA, Fac Ciencias, Dept Quim Organ, E-50009 Zaragoza, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 22期

关键词：

D O I：

10.1021/jo051572a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The cycloaddition reaction between C-(2-thiazolyl) nitrones and allylic alcohol takes place with complete exo selectivity when the reactions are carried out in the presence of 1 equiv of zinc triflate. The rate of the reaction is increased enormously under microwave irradiation. The use of a chiral dipolarophile allowed application of the methodology to the synthesis of a hitherto unknown enantiomerically pure isoxazolidinyl analogue of the C-nucleoside tiazofurin.

引用

页码：8991 / 9001

页数：11

共 52 条

[1]

[Anonymous], CHEM NUCLEOSIDES NUC

[2] Acylnitrene route to vicinal amino alcohols. Application to the synthesis of (-)-bestatin and analogues [J].

Bergmeier, SC ;

Stanchina, DM .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (08) :2852-2859

[3] CYANOHYDRIDOBORATE ANION AS A SELECTIVE REDUCING AGENT [J].

BORCH, RF ;

BERNSTEIN, MD ;

DURST, HD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (12) :2897-+

[4] THE CHIRAL SYNTHESIS OF THIAZOLE AMINO-ACID ENANTIOMERS [J].

BREDENKAMP, MW ;

HOLZAPFEL, CW ;

VANZYL, WJ .

SYNTHETIC COMMUNICATIONS, 1990, 20 (15) :2235-2249

[5] Synthesis of phosphonated carbocyclic 2′-oxa-3′-aza-nucleosides:: Novel inhibitors of reverse transcriptase [J].

Chiacchio, U ;

Balestrieri, E ;

Macchi, B ;

Iannazzo, D ;

Piperno, A ;

Rescifina, A ;

Romeo, R ;

Saglimbeni, M ;

Sciortino, MT ;

Valveri, V ;

Mastino, A ;

Romeo, G .

JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (05) :1389-1394

[6] Diastereoselective synthesis of homo-N,O-nucleosides [J].

Chiacchio, U ;

Genovese, F ;

Iannazzo, D ;

Librando, V ;

Merino, P ;

Rescifina, A ;

Romeo, R ;

Procopio, A ;

Romeo, G .

TETRAHEDRON, 2004, 60 (02) :441-448

[7] Enantioselective synthesis of N,O-psiconucleosides [J].

Chiacchio, U ;

Borrello, L ;

Iannazzo, D ;

Merino, P ;

Piperno, A ;

Rescifina, A ;

Richichi, B ;

Romeo, G .

TETRAHEDRON-ASYMMETRY, 2003, 14 (16) :2419-2425

[8] Diastereo- and enantioselective synthesis of N,O-nucleosides [J].

Chiacchio, U ;

Corsaro, A ;

Iannazzo, D ;

Piperno, A ;

Pistarà, V ;

Rescifina, A ;

Romeo, R ;

Sindona, G ;

Romeo, G .

TETRAHEDRON-ASYMMETRY, 2003, 14 (18) :2717-2723

[9] Isoxazolidine analogues of pseudouridine: a new class of modified nucleosides [J].

Chiacchio, U ;

Corsaro, A ;

Mates, J ;

Merino, P ;

Piperno, A ;

Rescifina, A ;

Romeo, G ;

Romeo, R ;

Tejero, T .

TETRAHEDRON, 2003, 59 (26) :4733-4738

[10]

Chiacchio U, 2002, EUR J ORG CHEM, V2002, P1206

← 1 2 3 4 5 6 →