A modular synthesis of the bis-tetrahydrofuran core of rolliniastatin from pyranoside precursors

被引：17

作者：

Ruan, ZM ^{[1
]}

Dabideen, D ^{[1
]}

Blumenstein, M ^{[1
]}

Mootoo, DR ^{[1
]}

机构：

[1] CUNY Hunter Coll, Dept Chem, New York, NY 10021 USA

来源：

TETRAHEDRON | 2000年 / 56卷 / 47期

基金：

美国国家卫生研究院;

关键词：

carbohydrates; iodoetherification; tetrahydrofuran; acetogenins;

D O I：

10.1016/S0040-4020(00)00878-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The iodoetherification of C6 allyllated 2,3-dideoxypyranosides has been shown to give cis-2,5-disubstituted tetrahydrofurans in high stereoselectivity. This result is applied to a modular synthesis of the bis-THF core of the acetogenin, rolliniastatin. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：9203 / 9211

页数：9

相关论文

共 38 条

[1] Annonaceous acetogenins: Recent progress [J].

Alali, FQ ;

Liu, XX ;

McLaughlin, JL .

JOURNAL OF NATURAL PRODUCTS, 1999, 62 (03) :504-540

[2]

[Anonymous], 1987, CARBON 13 NMR SPECTR

[3] STEREOCONTROLLED CYCLOFUNCTIONALIZATIONS OF DOUBLE-BONDS THROUGH HETEROCYCLIC INTERMEDIATES [J].

CARDILLO, G ;

ORENA, M .

TETRAHEDRON, 1990, 46 (10) :3321-3408

[4]

Casiraghi G., 1998, CHEMTRACTS ORG CHEM, V11, P803

[5] MODELING CHEMICAL-REACTIVITY .7. THE EFFECT OF A CHANGE IN RATE-LIMITING STEP ON THE STEREOSELECTIVITY OF ELECTROPHILIC ADDITION TO ALLYLIC ALCOHOLS AND RELATED CHIRAL ALKENES [J].

CHAMBERLIN, AR ;

MULHOLLAND, RL ;

KAHN, SD ;

HEHRE, WJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (03) :672-677

[6]

Emde U, 2000, EUR J ORG CHEM, V2000, P1889

[7] ANNONACEOUS ACETOGENINS - AN UPDATED REVIEW [J].

FANG, XP ;

RIESER, MJ ;

GU, ZM ;

ZHAO, GX ;

MCLAUGHLIN, JL .

PHYTOCHEMICAL ANALYSIS, 1993, 4 (01) :27-48

[8] UNSATURATED CARBOHYDRATES .11. ISOMERISATION AND DIMERISATION OF TRI-O-ACETYL-D-GLUCAL [J].

FERRIER, RJ ;

PRASAD, N .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1969, (04) :581-&

[9] SYNTHESES OF ACETOGENINS OF ANNONACEAE - A NEW CLASS OF BIOACTIVE POLYKETIDES [J].

FIGADERE, B .

ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (09) :359-365

[10] Replicative chirons: Stereoselective synthesis of oligo-tetrahydrofuranic lactones via C-glycosylation with [(trimethylsilyl)oxy]furan [J].

Figadere, B ;

Peyrat, JF ;

Cave, A .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (11) :3428-3429

← 1 2 3 4 →