Asymmetric Synthesis of (3R,5R)-3-((tert-Butyldimethylsily)oxy)-5-((Z)-2-Bromovinyl)-Tetrahydro-Furan-2-one,an Intermediate for the Synthesis of Fostriecin

作     者：Su Yun LIU Dao Fei HUANG Hai Hong HUANG Liang HUANG 

作者机构：Institute of Materia MedicaChinese Academy of Medical Science&Peking Union Medical CollegeBeijing 100050 

出 版 物：《Chinese Chemical Letters》 (中国化学快报(英文版))

年 卷 期：2000年第11卷第11期

页      面：957-960页

核心收录：

学科分类：07[理学] 0703[理学-化学] 

主　　题：Fostriecin dihydroxylation (-)-8-phenylmenthol asymmetric synthes 

摘      要：(3R,5R)-3-((tert-Butyldimethylsily)oxy)-5-((Z)-2-bromovinyl)-tetrahydro-furan-2-one, an intermediate for the synthesis of Fostriecin was achieved by intramolecular asymmetric induction in propene addition of (-)-8-phenylmenthyl glyoxylate followed by inversion of C3-hydroxyl group and Sharpless asymmetric dihydroxylation with simultaneous cyclization to give lactone 5. Then protection of C3-hydroxyl group and oxidation of the C6-primary hydroxyl group which reacted with Wittig reagent to yield the target compound 4.