First Synthesis of (+)-2,14-Deoxyalatol from -Santonin  

First Synthesis of (+)-2,14-Deoxyalatol from α-Santonin

作　　者：夏吾炯 孙良东 史雷 张书宇 涂永强 

机构地区：[1]Department of Chemistry & State Key Laboratory of Applied Organic Chemistry, Lanzhou University

出　　处：《Chinese Journal of Chemistry》2004年第4期377-383,共7页中国化学（英文版）

基　　金：theNationalNaturalScienceFoundationofChina(Nos.29925205;30271488;20021001and203900501).

摘　　要：A novel and general approach for synthesis of the multi-oxygenated dihydrofuran sesquiterpenes has been de-veloped starting from santonin. The key steps involve: the strategic acid-catalyzed double-bond shifting affording 4, the novel base-promoted epoxide rearrangement of 5 generating two key functionals (the C5-OH and the D7,11 dou-ble bond), and the stereoselective cyclization of tetrahydrofuran ring without pre-controlling the stereochemistry of C-7. As an example of this approach, synthesis of (+)-2,14-deoxyalatol was described in detail.A novel and general approach for synthesis of the multi-oxygenated dihydrofuran sesquiterpenes has been de-veloped starting from santonin. The key steps involve: the strategic acid-catalyzed double-bond shifting affording 4, the novel base-promoted epoxide rearrangement of 5 generating two key functionals (the C5-OH and the D7,11 dou-ble bond), and the stereoselective cyclization of tetrahydrofuran ring without pre-controlling the stereochemistry of C-7. As an example of this approach, synthesis of (+)-2,14-deoxyalatol was described in detail.

关 键 词：first synthesis dihydrofuran sesquiterpene (+)-2 14-deoxyalatol 

分 类 号：O621[理学—有机化学]