Improved and alternative synthesis of D- and L-cyclopentenone derivatives, the versatile intermediates for the synthesis of carbocyclic nucleosides

被引：102

作者：

Moon, HR

Choi, WJ

Kim, HO

Jeong, LS ^{[1
]}

机构：

[1] Ewha Womans Univ, Coll Pharm, Med Chem Lab, Seoul 120750, South Korea

[2] Seoul Natl Univ, Div Chem & Mol Engn, Seoul 151742, South Korea

来源：

TETRAHEDRON-ASYMMETRY | 2002年 / 13卷 / 11期

关键词：

D O I：

10.1016/S0957-4166(02)00316-6

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Improved and alternative syntheses Of D- and L-cyclopentenone derivatives were achieved in six steps from D-ribose via ring-closing metathesis (RCM) reaction as a key step. These derivatives serve as very versatile intermediates for the synthesis of carbocyclic nucleosides. (C) 2002 Elsevier Science Ltd. All rights reserved.

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页码：1189 / 1193

页数：5

相关论文

共 26 条

[1]

ACEVEDO OL, 1986, NUCL ACID CHEM 3, P35

[2] SYNTHESIS OF CARBOCYCLIC NUCLEOSIDES [J].

AGROFOGLIO, L ;

SUHAS, E ;

FARESE, A ;

CONDOM, R ;

CHALLAND, SR ;

EARL, RA ;

GUEDJ, R .

TETRAHEDRON, 1994, 50 (36) :10611-10670

[3]

[Anonymous], 2004, ORGANIC CHEM DRUG DE

[4] SYNTHESIS OF ENANTIOMERICALLY PURE (2'R,5'S)-(-)-1-[2-(HYDROXYMETHYL)OXATHIOLAN-5-YL]CYTOSINE AS A POTENT ANTIVIRAL AGENT AGAINST HEPATITIS-B VIRUS (HBV) AND HUMAN-IMMUNODEFICIENCY-VIRUS (HIV) [J].

BEACH, JW ;

JEONG, LS ;

ALVES, AJ ;

POHL, D ;

KIM, HO ;

CHANG, CN ;

DOONG, SL ;

SCHINAZI, RF ;

CHENG, YC ;

CHU, CK .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (08) :2217-2219

[5] SYNTHESIS OF CHIRAL CARBOCYCLIC NUCLEOSIDES [J].

BORTHWICK, AD ;

BIGGADIKE, K .

TETRAHEDRON, 1992, 48 (04) :571-623

[6] Syntheses of D- and L-cyclopentenone derivatives using ring-closing metathesis: Versatile intermediates for the synthesis of D- and L-carbocyclic nucleosides [J].

Choi, WJ ;

Park, JG ;

Yoo, SJ ;

Kim, HO ;

Moon, HR ;

Chun, MW ;

Jung, YH ;

Jeong, LS .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (19) :6490-6494

[7] USE OF 2'-FLUORO-5-METHYL-BETA-L-ARABINOFURANOSYLURACIL AS A NOVEL ANTIVIRAL AGENT FOR HEPATITIS-B VIRUS AND EPSTEIN-BARR-VIRUS [J].

CHU, CK ;

MA, TW ;

SHANHMUGANATHAN, K ;

WANG, CG ;

XIANG, YJ ;

PAI, SB ;

YAO, GQ ;

SOMMADOSSI, JP ;

CHENG, YC .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1995, 39 (04) :979-981

[8] THE SEPARATED ENANTIOMERS OF 2'-DEOXY-3'-THIACYTIDINE (BCH-189) BOTH INHIBIT HUMAN-IMMUNODEFICIENCY-VIRUS REPLICATION INVITRO [J].

COATES, JAV ;

CAMMACK, N ;

JENKINSON, HJ ;

MUTTON, IM ;

PEARSON, BA ;

STORER, R ;

CAMERON, JM ;

PENN, CR .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1992, 36 (01) :202-205

[9] New developments in the enantioselective synthesis of cyclopentyl carbocyclic nucleosides [J].

Crimmins, MT .

TETRAHEDRON, 1998, 54 (32) :9229-9272

[10] 1592U89, a novel carbocyclic nucleoside analog with potent, selective anti-human immunodeficiency virus activity [J].

Daluge, SM ;

Good, SS ;

Faletto, MB ;

Miller, WH ;

StClair, MH ;

Boone, LR ;

Tisdale, M ;

Parry, NR ;

Reardon, JE ;

Dornsife, RE ;

Averett, DR ;

Krenitsky, TA .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1997, 41 (05) :1082-1093