Stereoselective entry to 1′-C-branched 4′-thionucleosides from 4′-thiofuranoid glycal:: synthesis of 4′-thioangustmycin C

被引：21

作者：

Haraguchi, K ^{[1
]}

Takahashi, H ^{[1
]}

Tanaka, H ^{[1
]}

机构：

[1] Showa Univ, Sch Pharmaceut Sci, Shinagawa Ku, Tokyo 1428555, Japan

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 32期

关键词：

nucleosides; glycals; glycosidation; antibiotics;

D O I：

10.1016/S0040-4039(02)01131-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A stereoselective synthetic method for the synthesis of novel 1'-C-carbon-substituted 4'-thionucleosides has been developed. The present method consists of the following steps: (1) preparation of the 1-C-carbon-substituted 4-thiofuranoid glycals based on lithiation, and (2) NIS- or PhSeCl-initiated stereoselective glycosidation to these 1-substituted glycals. This synthetic sequence enabled us to synthesize the 4'-thio analogue of antitumor antibiotic angustmycin (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：5657 / 5660

页数：4

共 18 条

[1]

BRANALT J, 1994, J ORG CHEM, V59, P1783

[2] THE SYNTHESIS AND ANTIVIRAL ACTIVITY OF SOME 4'-THIO-2'-DEOXY NUCLEOSIDE ANALOGS [J].

DYSON, MR ;

COE, PL ;

WALKER, RT .

JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (09) :2782-2786

[3] PREPARATION OF C-ARYL GLUCALS VIA THE PALLADIUM-CATALYZED COUPLING OF METALATED AROMATICS WITH 1-IODO-3,4,6-TRI-O-(TRIISOPROPYLSILYL)-D-GLUCAL [J].

FRIESEN, RW ;

LOO, RW .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (16) :4821-4823

[4] PUMMERER REARRANGEMENT OF SELENIUM-CONTAINING URACIL NUCLEOSIDES [J].

HARAGUCHI, K ;

SAITO, S ;

TANAKA, H ;

MIYASAKA, T .

NUCLEOSIDES & NUCLEOTIDES, 1992, 11 (2-4) :483-493

[5] Electrophilic addition to 4-thio furanoid glycal:: a highly stereoselective entry to 2′-deoxy-4′-thio pyrimidine nucleosides [J].

Haraguchi, K ;

Nishikawa, A ;

Sasakura, E ;

Tanaka, H ;

Nakamura, K ;

Miyasaka, T .

TETRAHEDRON LETTERS, 1998, 39 (22) :3713-3716

[6]

HARAGUCHI K, 1998, NUCL ACIDS S SERIES, V30, P17

[7]

HARAGUCHI K, IN PRESS J ORG CHEM

[8] Synthesis of enantiomerically pure 9-[(1′R,2′R,3′S)-bis(hydroxymethyl)thietan-1′-yl] adenine, 3′-thio analog of oxetanocin A [J].

Ichikawa, E ;

Yamamura, S ;

Kato, K .

TETRAHEDRON LETTERS, 1999, 40 (41) :7385-7388

[9] Novel triazole 2′-deoxy-4′-thionucleosides:: Stereoselective synthesis and biological evaluation [J].

Inguaggiato, G ;

Jasamai, M ;

Smith, JE ;

Slater, M ;

Simons, C .

NUCLEOSIDES & NUCLEOTIDES, 1999, 18 (03) :457-467

[10]

KAGA D, 2001, NUCL ACIDS RES S, V1, P103

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