A potentially divergent and rapid route to analogues of deoxycyclitols, pentopyranoses, 6-deoxyhexoses, and hexoses

被引：24

作者：

Audouard, C ^{[1
]}

Fawcett, J ^{[1
]}

Griffith, GA ^{[1
]}

Kérourédan, E ^{[1
]}

Miah, A ^{[1
]}

Percy, JM ^{[1
]}

Yang, HL ^{[1
]}

机构：

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

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 23期

关键词：

D O I：

10.1021/ol0482902

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Direct precursors to analogues of pentopyranoses, 6-deoxyhexoses, and hexoses, in which a CF2 center replaces the pyranose oxygen, have been synthesized rapidly from trifluoroethanol. A simple scaleable allylation reaction delivers ethers which undergo dehydrofluorination/metalation, followed by addition to either acrolein or cinnamaldehyde, to afford allylic alcohols. Fluorine-assisted [3,3]-rearrangement followed by reduction with sodium borohydride delivers diols, which undergo RCM smoothly to afford cyclohexene diols.

引用

页码：4269 / 4272

页数：4

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