Highly-functionalised difluorinated (hydroxymethyl)conduritol analogues via the Diels-Alder reactions of a difluorinated dienophile

被引：20

作者：

Arany, A

Crowley, PJ

Fawcett, J

Hursthouse, MB

Kariuki, BM

Light, ME

Moralee, AC

Percy, JM

Salafia, V

机构：

[1] Univ Leicester, Dept Chem, Leicester LE1 7RH, Leics, England

[2] Univ Birmingham, Sch Chem Sci, Birmingham B15 2TT, W Midlands, England

[3] Syngenta Ltd, Jealotts Hill Int Res Ctr, Bracknell RG42 6EY, Berks, England

[4] Univ Southampton, Dept Chem, EPSRC, Natl Xray Crystallog Serv, Southampton SO17 1BJ, Hants, England

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2004年 / 2卷 / 04期

关键词：

D O I：

10.1039/b314314g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A difluorodienophile, synthesised using a Stille coupling reaction underwent tin(IV)-catalysed cycloaddition with three furans to afford oxa[2.2.1]bicycloheptenes in good yield. Reduction of ester and carbamate carbonyl groups and diol protection as the acetonide set the stage for palladium-catalysed hydrostannylation in two cases. Treatment of the stannanes with methyllithium triggered ring-opening to afford highly-functionalised difluorinated cyclohexenols which could be deprotected to afford (hydroxymethyl)conduritol analogues.

引用

页码：455 / 465

页数：11

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[31] Synthesis of 2′,3′-dideoxy-3′,3′-difluoro and 2′,3′-dideoxy-2′,2′-difluoropyranosyl nucleosides analogues of gemcitabine [J].