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A Carbohydrate-Based Approach for the Total Synthesis of (-)-Dinemasone B, (+)-4a-epi-Dinemasone B, (-)-7-epi-Dinemasone B, and (+)-4a,7-Di-epi-dinemasone B
Xue, Xiaochao; Yin, Zhaojun; Meng, Xiangbao; Li, Zhongjun
刊名JOURNAL OF ORGANIC CHEMISTRY
2013-09-20
DOI10.1021/jo4015694
78期:18页:9354-9365
收录类别SCI ; IC ; CCR
文章类型Article
WOS标题词Science & Technology
类目[WOS]Chemistry, Organic
研究领域[WOS]Chemistry
关键词[WOS]CATALYTIC ENANTIOSELECTIVE REDUCTION ; CHIRAL LEWIS-ACID ; STEREOCHEMICAL PURITY ; BIOLOGICAL EVALUATION ; ASYMMETRIC REDUCTION ; GENERAL-SYNTHESIS ; AQUEOUS-MEDIA ; ONE-STEP ; KETONES ; OXIDATION
英文摘要

(-)-Dinemasone B was isolated by Krohn and co-workers from a culture of the endophytic fungus Dinemasporium strigosum and has shown promising antimicrobial activity. Described herein is the first total synthesis of (-)-dinemasone B, (+)-4a-epi-dinemasone B, (-)-7-epi-dinemasone B, and (+)-4a,7-di-epi-dinemasone B. Their absolute configurations were also determined. The developed synthesis features a stereoselective reduction of C-glycosidic ketone, lactonization, and E-olefination of aldehyde starting from D-glucose.

语种英语
WOS记录号WOS:000330159500045
项目编号81273369 ; 21072016 ; 21072017 ; 2012CB822100 ; 2012ZX09502001-001
资助机构National Natural Science Foundation of China (NSFC) ; National Basic Research Program of China (973 Program) ; National Key Technology R&amp ; D Program "New Drug Innovation" of China
引用统计
被引频次:4[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/400002259/52698
专题北京大学药学院_化学生物学系
作者单位Peking Univ, Sch Pharmaceut Sci, Dept Biol Chem, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China
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GB/T 7714
Xue, Xiaochao,Yin, Zhaojun,Meng, Xiangbao,et al. A Carbohydrate-Based Approach for the Total Synthesis of (-)-Dinemasone B, (+)-4a-epi-Dinemasone B, (-)-7-epi-Dinemasone B, and (+)-4a,7-Di-epi-dinemasone B[J]. JOURNAL OF ORGANIC CHEMISTRY,2013,78(18):9354-9365.
APA Xue, Xiaochao,Yin, Zhaojun,Meng, Xiangbao,&Li, Zhongjun.(2013).A Carbohydrate-Based Approach for the Total Synthesis of (-)-Dinemasone B, (+)-4a-epi-Dinemasone B, (-)-7-epi-Dinemasone B, and (+)-4a,7-Di-epi-dinemasone B.JOURNAL OF ORGANIC CHEMISTRY,78(18),9354-9365.
MLA Xue, Xiaochao,et al."A Carbohydrate-Based Approach for the Total Synthesis of (-)-Dinemasone B, (+)-4a-epi-Dinemasone B, (-)-7-epi-Dinemasone B, and (+)-4a,7-Di-epi-dinemasone B".JOURNAL OF ORGANIC CHEMISTRY 78.18(2013):9354-9365.
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