Scalable Synthesis of Cyclocitrinol

被引：61
|
作者：
Wang, Yu [1 ]
Ju, Wei [1 ]
Tian, Hailong [1 ]
Tian, Weisheng [1 ]
Gui, Jinghan [1 ]
机构：
[1] Chinese Acad Sci, Univ Chinese Acad Sci, Shanghai Inst Organ Chem, CAS Key Lab Synthet Chem Nat Subst,Ctr Excellence, 345 Lingling Rd, Shanghai 200032, Peoples R China
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2018年 / 140卷 / 30期
基金：
中国国家自然科学基金;
关键词：
UNUSUAL C25 STEROIDS; PENICILLIUM-CITRINUM; FUNGUS; REARRANGEMENT; NORCARADIENE; CASCADE; RINGS; CORE;
D O I：
10.1021/jacs.8b06444
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A 10-step synthesis of the C25 steroid natural product cyclocitrinol from inexpensive, commercially available pregnenolone is reported. This synthesis features a biomimetic cascade rearrangement to efficiently construct the challenging bicyclo[4.4.1] A/B ring system, which enabled a gram-scale synthesis of the bicyclo[4.4.1] enone intermediate 18 in only nine steps. This work also provides experimental support for the biosynthetic origin of cyclocitrinol.
引用
收藏
页码：9413 / 9416
页数：4
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