The synthesis of carbohydrate-derived acylsilanes and their intramolecular free radical cyclizations with the formation of polyoxygenated cyclopentanes
Resource
Tetrahedron Letters 50 (27): 3805-3808
Journal
Tetrahedron Letters
Pages
3805-3808
Date Issued
2009
Date
2009
Author(s)
Chang, Che-Chien
Kuo, Yu-Hsien
Tsai, Yeun-Min
Abstract
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. © 2009 Elsevier Ltd. All rights reserved.
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journal article
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