Transannular [4+3] Cycloadditions of Macrocyclic Epoxy Ketones

被引：9
作者：
Chan, Diana [1 ]
Chen, Yu [1 ]
Low, Kam-Hung [1 ]
Chiu, Pauline [1 ]
机构：
[1] Univ Hong Kong, State Key Lab Synthet Chem, Dept Chem, Pokfulam Rd, Hong Kong, Hong Kong, Peoples R China
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2018年 / 24卷 / 10期
关键词：
cycloadditions; cycloisomerization; macrocycles; polycyclic; transannular; RING-CLOSING METATHESIS; DIELS-ALDER REACTION; ENOLSILANES; GUANACASTEPENE; SKELETON;
D O I：
10.1002/chem.201800019
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Transannular [4+3] cycloadditions of dienophiles derived from macrocyclic epoxy ketones produce fused ring systems having central cycloheptane subunits. In some cases, the base directly induced cycloisomerization of the epoxy ketones to yield the cycloadducts; in others, the epoxy ketones were transformed into their corresponding enolsilanes before undergoing cycloaddition. Enantiomerically enriched tricyclic arrays were obtained from cycloadditions starting from optically pure epoxy ketones.
引用
收藏
页码：2375 / 2378
页数：4
相关论文
共 44 条
[21]   Transannular [4+2] Cycloaddition Reactions of Cobalt-Complexed Macrocyclic Dienynes [J].
Karabiyikoglu, Sedef ;
Merlic, Craig A. .
ORGANIC LETTERS, 2015, 17 (16) :4086-4089
[22]  
Krenske E. H., 2015, ANGEW CHEM, V127, P7530
[23]   Concerted Ring Opening and Cycloaddition of Chiral Epoxy Enolsilanes with Dienes [J].
Krenske, Elizabeth H. ;
Lam, Sarah ;
Ng, Jerome P. L. ;
Lo, Brian ;
Lam, Sze Kui ;
Chiu, Pauline ;
Houk, Kendall N. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (25) :7422-7425
[24]   Formal Total Synthesis of (+)-Cortistatins A and J [J].
Kuang, Liping ;
Liu, Lok Lok ;
Chiu, Pauline .
CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (41) :14287-14291
[25]   Enantiomerically Enriched (4+3) Cycloadducts from Optically Active Epoxy Enolsilanes [J].
Lam, Sarah ;
Lo, Brian ;
Wong, Wing-Tak ;
Chiu, Pauline .
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 1 (01) :30-33
[26]  
Lam SYY, 2014, METHODS AND APPLICATIONS OF CYCLOADDITION REACTIONS IN ORGANIC SYNTHESES, P565
[27]   Biomimetic synthesis of (-)-longithorone A [J].
Layton, ME ;
Morales, CA ;
Shair, MD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (05) :773-775
[28]  
Lo B., 2012, ANGEW CHEM, V124, P12286
[29]   Asymmetric (4+3) Cycloadditions of Enantiomerically Enriched Epoxy Enolsilanes [J].
Lo, Brian ;
Lam, Sarah ;
Wong, Wing-Tak ;
Chiu, Pauline .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (48) :12120-12123
[30]   (4+3) Cycloaddition Reactions of Nitrogen-Stabilized Oxyallyl Cations [J].
Lohse, Andrew G. ;
Hsung, Richard P. .
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (14) :3812-3822
12345