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

页码：9413 / 9416

页数：4

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