A concise enantioselective pathway to carbocyclic nucleoside: Asymmetric synthesis of carbocyclic moiety of carbovir

被引：13

作者：

Tanimori, S

Tsubota, M

He, MQ

Nakayama, M

机构：

[1] Department of Applied Biochemistry, College of Agriculture, Osaka Prefecture University, Sakai, Osaka 593

来源：

SYNTHETIC COMMUNICATIONS | 1997年 / 27卷 / 14期

关键词：

D O I：

10.1080/00397919708004098

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(-)-Trans-4-t-butyldimethylsilyloxymethyl-2-cyclopentenol (13), a key intermediate for the synthesis of (-)-carbovir (15), was synthesized by using enantioselective bicyclic ring construction of chiral alpha-diazo-beta-keto ester 3 catalyzed by rhodium (II) acetate.

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页码：2371 / 2378

页数：8

相关论文

共 13 条

[1] AN ASYMMETRIC-SYNTHESIS OF (-)-CARBOVIR [J].

ASAMI, M ;

TAKAHASHI, J ;

INOUE, S .

TETRAHEDRON-ASYMMETRY, 1994, 5 (09) :1649-1652

[2] An efficient asymmetric approach to carbocyclic nucleosides: Asymmetric synthesis of 1592U89, a potent inhibitor of HIV reverse transcriptase [J].

Crimmins, MT ;

King, BW .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (13) :4192-4193

[3] ALPHA-HYDROXY ESTERS AS CHIRAL AUXILIARIES IN ASYMMETRIC CYCLOPROPANATIONS BY RHODIUM(II)-STABILIZED VINYLCARBENOIDS [J].

DAVIES, HML ;

HUBY, NJS ;

CANTRELL, WR ;

OLIVE, JL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (21) :9468-9479

[4] ALKYLATION OF DIANIONS OF BETA-KETO-ESTERS [J].

HUCKIN, SN ;

WEILER, L .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (04) :1082-1087

[5]

KONDO K, 1976, TETRAHEDRON LETT, P4489

[6] INTRAMOLECULAR CYCLOPROPANATION USING IODONIUM YLIDES - THE 3,5-CYCLOVITAMIN-D RING-A SYNTHON [J].

MORIARTY, RM ;

KIM, J ;

GUO, LA .

TETRAHEDRON LETTERS, 1993, 34 (26) :4129-4132

[7] A GENERAL-METHOD FOR THE SYNTHESIS OF 3,5-CYCLOVITAMIN-D3 AND DERIVATIVES - A STEREOSELECTIVE SYNTHESIS OF VITAMIN-D3 [J].

NEMOTO, H ;

WU, XM ;

KUROBE, H ;

MINEMURA, K ;

IHARA, M ;

FUKUMOTO, K ;

KAMETANI, T .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (06) :1185-1190

[8] DIASTEREOFACE-DISCRIMINATIVE METAL COORDINATION IN ASYMMETRIC-SYNTHESIS - D-PANTOLACTONE AS PRACTICAL CHIRAL AUXILIARY FOR LEWIS ACID-CATALYZED DIELS-ALDER REACTIONS [J].

POLL, T ;

SOBCZAK, A ;

HARTMANN, H ;

HELMCHEN, G .

TETRAHEDRON LETTERS, 1985, 26 (26) :3095-3098

[9] ENANTIOSELECTIVE RING CONSTRUCTION WITH CONTROL OF SIDE-CHAIN STEREOCHEMISTRY - SYNTHESIS OF (+)-ISONEONEPETALACTONE [J].

TABER, DF ;

AMEDIO, JC ;

RAMAN, K .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (13) :2984-2990

[10] A NEW NUCLEOPHILIC RING-OPENING OF AN ACTIVATED CYCLOPROPANE AND A FORMAL SYNTHESIS OF(+/-)-CARBOVIR [J].

TANIMORI, SJ ;

TSUBOTA, M ;

HE, MQ ;

NAKAYAMA, M .

BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 1995, 59 (11) :2091-2093