|
单族毒素Tenuipesine A的全合成研究
Toward the total synthesis of Tenuipesine A
查看参考文献8篇
文摘
|
以1,3-环己二酮和香叶醇为起始原料,通过12步反应,合成了具有3/6/5三环骨架的关键中间体4.其中关键反应有:[3,3]重排反应一步构筑两个相邻的全碳季碳中心;Grubbs-2nd催化剂催化的关环复分解反应构筑5元环;Simmons-Smith环丙烷化反应构筑3元环. |
其他语种文摘
|
A key intermediate 4 with 3/6/5 tricyclic core was synthesized in 12 steps from 1, 3-cyclohexanedione and geraniol, paving the way for the total synthesis of Tenuipesine A. The developed synthetic strategy featured a [3, 3] rearrangment reaction to introduce two contiguous all-carbon quaternary centers; a ring closing metathesis reaction was catalyzed by Grubbs-2nd catalyst to form a five-membered ring; and a Simmons-Smith reaction was utilized to construct a cyclopropane moiety. |
来源
|
兰州大学学报. 自然科学版
,2012,48(5):135-138 【核心库】
|
关键词
|
Tenuipesine A
;
全碳季碳
;
关环复分解反应
;
Simmons-Smith环丙烷化反应
|
地址
|
兰州大学化学化工学院, 功能有机分子化学国家重点实验室, 兰州, 730000
|
语种
|
中文 |
ISSN
|
0455-2059 |
学科
|
化学 |
基金
|
国家自然科学基金项目
;
国家973计划
;
卫生部国家重点科技项目“重大新药开发”项目
;
兰州大学高等学校学科创新引智计划(111计划)项目
|
文献收藏号
|
CSCD:4663214
|
参考文献 共
8
共1页
|
1.
Kikuchi H. A novel carbon skeletal trichothecane, tenuipesine a, isolated from an entomopathogenic fungus, Paecilomyces tenuipes.
Org Lett,2004,6(24):4531-4533
|
被引
7
次
|
|
|
|
2.
Grubbs R H. Ring-closing metathesis and related processes in organic synthesis.
Acc Chem Res,1995,28(11):446-452
|
被引
10
次
|
|
|
|
3.
Schuster M. Olefin metathesis in organic chemistry.
Angew Chem Int Ed,1997,36(19):2036-2056
|
被引
3
次
|
|
|
|
4.
Simmons H E. A new synthesis of cyclopropanes from olefins.
J Am Chem Soc,1958,80(19):5323-5324
|
被引
12
次
|
|
|
|
5.
Simmons H E. A new synthesis of cyclopropanes.
J Am Chem Soc,1959,81(16):4256-4264
|
被引
6
次
|
|
|
|
6.
Furukawa J. A novel route to cyclopropanes from olefins.
Tetrahedron Lett,1966,7(28):3353-3354
|
被引
1
次
|
|
|
|
7.
Uyeda C. Catalytic enantioselective claisen rearrangments of O-Allyl-Ketoesters.
Angew Chem Int Ed,2010,49(50):9753-9756
|
被引
2
次
|
|
|
|
8.
Mitsunobu O. Preparation of esters of carboxylic and phosphoric acid via quaternary phosphonium salts.
Bull Chem Soc Jpn,1967,40(10):2380-2382
|
被引
14
次
|
|
|
|
|
|