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A facile asymmetric synthesis of (+)-eldanolide
Kong, Linglong; Zhuang, Zeyang; Chen, Qingshou; Deng, Haibing; Tang, Zhiyong; Jia, Xueshun; Li, Yulin; Zhai, Hongbin
刊名TETRAHEDRON-ASYMMETRY
2007-03-12
DOI10.1016/j.tetasy.2007.01.035
18期:4页:451-454
收录类别SCI ; IC ; CCR
文章类型Article
WOS标题词Science & Technology
类目[WOS]Chemistry, Inorganic & Nuclear ; Chemistry, Organic ; Chemistry, Physical
研究领域[WOS]Chemistry
关键词[WOS]SUGAR-CANE BORER ; ELDANA-SACCHARINA WLK ; WING GLAND PHEROMONE ; STEREOSELECTIVE-SYNTHESIS ; (-)-CIS-WHISKEY LACTONE ; EFFICIENT SYNTHESIS ; PRACTICAL METHOD ; ENANTIOMERS ; ELDANOLIDE ; SEGMENT
英文摘要

The monoterpenoid pheromone (+)-eldanolide, a long range sex attractant, has been synthesized in four steps from the chiral 2,3-epoxy alcohol 4 in 36% overall yield. Our synthetic strategy features the formation of a 1,3-diol by regio- and stereoselective ring opening of 2,3-epoxy alcohol 4, an intermediate easily available from Sharpless asymmetric epoxidation. Other key steps include one carbon elongation, saponification, and lactonization. The present work constitutes a general method for the rapid synthesis of a number of related gamma-lactone natural products. (c) 2007 Elsevier Ltd. All rights reserved.

语种英语
WOS记录号WOS:000245836500003
引用统计
被引频次:10[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.bjmu.edu.cn/handle/400002259/54563
专题北京大学药学院
作者单位1.Shanghai Univ, Dept Chem, Shanghai 200444, Peoples R China
2.Lanzhou Univ, Inst Organ Chem, Lanzhou 730000, Peoples R China
3.Chinese Acad Sci, Shanghai Inst Organ Chem, Lab Modern Synth Organ Chem, Shanghai 200032, Peoples R China
4.Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China
5.Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Beijing 100083, Peoples R China
6.Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
推荐引用方式
GB/T 7714
Kong, Linglong,Zhuang, Zeyang,Chen, Qingshou,et al. A facile asymmetric synthesis of (+)-eldanolide[J]. TETRAHEDRON-ASYMMETRY,2007,18(4):451-454.
APA Kong, Linglong.,Zhuang, Zeyang.,Chen, Qingshou.,Deng, Haibing.,Tang, Zhiyong.,...&Zhai, Hongbin.(2007).A facile asymmetric synthesis of (+)-eldanolide.TETRAHEDRON-ASYMMETRY,18(4),451-454.
MLA Kong, Linglong,et al."A facile asymmetric synthesis of (+)-eldanolide".TETRAHEDRON-ASYMMETRY 18.4(2007):451-454.
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