Stereoselective synthesis of highly substituted 8-oxabicyclo[3.2.1]octanes and聽2,7-dioxatricyclo[4.2.1.0^3,8]nonanes

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• 作者：Dmitry A. Khlevin^a ; ^{khlevindmitry@yahoo.com} ; Sergey E. Sosonyuk^a ; Marina V. Proskurnina^a ; Nikolay S. Zefirov^a ; ^b
• 关键词：8-Oxabicyclo[3.2.1]octanes ; 2 ; 7-Dioxatricyclo[4.2.1.03 ; 8]nonanes ; Hydride reduction ; Transannular hydroxycyclization ; Diastereoselectivity
• 刊名：Tetrahedron
• 出版年：2012
• 期刊代码：107_00404020
• 类别：ch
• 出版时间：22 July, 2012
• 卷：68
• 期：29
• 页码：5785-5792
• 文件大小：641 K

摘要

The synthesis of new polyhydroxylated 8-oxabicyclo[3.2.1]octanes and 2,7-dioxatricyclo[4.2.1.0^3,8]nonanes is described. These structures is an interesting synthetic blocks for potential bioactive molecules. The precursor, 3-chloro-8-oxabicyclo[3.2.1]oct-6-ene-2,4-dione was obtained from reaction of tetrachlorocyclopropene with furan, then it was involved in carbonyl groups reduction and double bond oxidation, resulted in the formation of a polyhydroxylated derivatives, differently substituted at C-3 position, with five new stereocenters.

Using intramolecular transannular hydroxycyclization, bicyclic epoxy diacetate was transformed into 2,7-dioxatricyclo[4.2.1.0^3,8]nonane in high yield through an alkoxide intermediate. Compounds thus obtained have a structure close to certain molecules with antitumor and glycosidase inhibitors activity.