Synthesis of Cyclocitrinol Skeleton via a Carbocation Rearrangement

被引：7

作者：

Liu, Tao ^{[1
]}

Yan, Yubo ^{[2
]}

Ma, Haiyan ^{[1
]}

Ding, Kai ^{[3
]}

机构：

[1] E China Univ Sci & Technol, Lab Organometall, Shanghai 200237, Peoples R China

[2] Shanghai Normal Univ, Lab Resource Chem, Shanghai 200234, Peoples R China

[3] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Synthet Chem Nat Subst, Shanghai 200032, Peoples R China

来源：

CHINESE JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 34卷 / 09期

关键词：

steroids; mitsunobu reaction; cyclocitrinol; carbocation rearrangement; STEROIDS;

D O I：

10.6023/cjoc201404033

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cyclocitrinol featured a unique bridged bicyclic skeletons, which may be constructed via SmI2-mediated reaction from a highly strained norcarenone. Herein, using commercially available 19-hydroxy-androstane as starting material, the norcarenone intermediate was synthesized via a novel homoallylic carbocation rearrangement, which was transformed into the core of cyclocitrinols.

引用

页码：1793 / 1799

页数：7

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