The synthesis of carbohydrate-derived acylsilanes and their intramolecular free radical cyclizations with the formation of polyoxygenated cyclopentanes

被引：11
|
作者：
Chang, Che-Chien [1 ]
Kuo, Yu-Hsien [1 ]
Tsai, Yeun-Min [1 ]
机构：
[1] Natl Taiwan Univ, Dept Chem, Taipei 106, Taiwan
来源：
TETRAHEDRON LETTERS | 2009年 / 50卷 / 27期
关键词：
Acylsilane; Radical cyclization; Polyoxygenated cyclopentanes; BROOK REARRANGEMENT; CARBON RADICALS; SILYL; CARBOCYCLES; DERIVATIVES; CONVERSION; OXIDATION; ALCOHOLS; ROUTE; DIMETHYLSULFOXIDE;
D O I：
10.1016/j.tetlet.2009.04.032
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A convenient way for the synthesis of acylsilanes from arabinose, lyxose, and ribose is developed. All the chiral centers of the carbohydrate templates are conserved, and only the reducing end is transformed into the acylsilane functional group. The non-reducing end of the templates can be converted into a bromide. These bromo acylsilanes undergo efficient intramolecular radical cyclizations to give polyoxygenated cyclopentanes. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3805 / 3808
页数：4
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