First synthesis of (-)-neplanocin C

被引：25

作者：

Comin, MJ ^{[1
]}

Rodriguez, JB ^{[1
]}

机构：

[1] Univ Buenos Aires, Fac Ciencias Exactas & Nat, Dept Quim Organ, RA-1428 Buenos Aires, DF, Argentina

来源：

TETRAHEDRON | 2000年 / 56卷 / 27期

关键词：

carbohydrates; nucleosides; purines; enantiomeric purity;

D O I：

10.1016/S0040-4020(00)00379-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(-)-Neplanocin C (4), a minor component of the neplanocin family of antibiotics and a lead drug for the design of several conformationally constrained nucleosides analogues, was enantioselectively synthesized starting from D-ribono-1,4-lactone via a convergent approach in twelve steps. The proton NMR spectrum of 4 was in agreement with the corresponding natural product. Calculated coupling constants obtained from ab initio molecular modeling studies and from previously published X-ray structure of neplanocin C also corresponded to the spectroscopic data. (C) 2000 Elsevier Science Ltd. All rights reserved.

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收藏

页码：4639 / 4649

页数：11

相关论文

共 58 条

[1] 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

[2]

Altmann K. -H., 1994, TETRAHEDRON LETT, V35, P7265

[3] 4',6'-METHANO CARBOCYCLIC THYMIDINE - A CONFORMATIONALLY CONSTRAINED BUILDING-BLOCK FOR OLIGONUCLEOTIDES [J].

ALTMANN, KH ;

KESSELRING, R ;

FRANCOTTE, E ;

RIHS, G .

TETRAHEDRON LETTERS, 1994, 35 (15) :2331-2334

[4] CONFORMATIONAL-ANALYSIS OF SUGAR RING IN NUCLEOSIDES AND NUCLEOTIDES - NEW DESCRIPTION USING CONCEPT OF PSEUDOROTATION [J].

ALTONA, C ;

SUNDARALINGAM, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (23) :8205-+

[5]

[Anonymous], 2004, ORGANIC CHEM DRUG DE

[6] SYNTHESIS OF (-)-NEPLANOCIN A FROM (R,R)-TARTARIC ACID [J].

BESTMANN, HJ ;

ROTH, D .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (01) :99-100

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

BORTHWICK, AD ;

BIGGADIKE, K .

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

[8] SYNTHESIS OF CARBOCYCLIC ANALOGS OF GUANOSINE 5'-(BETA-L-FUCOPYRANOSYL DIPHOSPHATE) (GDP-FUCOSE) AS POTENTIAL INHIBITORS OF FUCOSYLTRANSFERASES [J].

CAI, S ;

STROUD, MR ;

HAKOMORI, S ;

TOYOKUNI, T .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (25) :6693-6696

[9] STUDIES ON STRUCTURALLY SIMPLE ALPHA,BETA-BUTENOLIDES .2. (-)-(S)-GAMMA-HYDROXYMETHYL-ALPHA,BETA-BUTENOLIDE AND DERIVATIVES FROM D-RIBONOLACTONE EFFICIENT SYNTHESIS OF (-)-RANUNCULIN [J].

CAMPS, P ;

CARDELLACH, J ;

FONT, J ;

ORTUNO, RM ;

PONSATI, O .

TETRAHEDRON, 1982, 38 (15) :2395-2402

[10] Synthesis of C-5′-nor-dideoxycarbanucleosides structurally related to neplanocin C [J].

Comin, MJ ;

Pujol, CA ;

Damonte, EB ;

Rodriguez, JB .

NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 1999, 18 (10) :2219-2231

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