Biomimetic Syntheses from Squalene-Like Precursors: Synthesis of ent-Abudinol B and Reassessment of the Structure of Muzitone

被引：23

作者：

Boone, Matthew A. ^{[1
]}

Tong, Rongbiao ^{[1
]}

McDonald, Frank E. ^{[1
]}

Lense, Sheri ^{[1
]}

Cao, Rui ^{[1
]}

Hardcastle, Kenneth I. ^{[1
]}

机构：

[1] Emory Univ, Dept Chem, Atlanta, GA 30322 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2010年 / 132卷 / 14期

基金：

美国国家科学基金会;

关键词：

CATION-STABILIZING AUXILIARIES; EPOXIDE-OPENING CASCADES; SIMPLE ENANTIOSELECTIVE SYNTHESIS; POLYENE CYCLIZATIONS; FLUORINE ATOM; ASYMMETRIC EPOXIDATION; TRITERPENES; REARRANGEMENT; DITERPENOIDS; POLYPRENOIDS;

D O I：

10.1021/ja1006806

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We achieved the stereoselective syntheses of two different structural patterns corresponding to the enantiomers of the marine natural products abudinol B and muzitone, by developing two-directional tandem biomimetic cyclizations of polyepoxides of squalene analogues in which one alkene was functionalized as an enolsilane. In the course of this work, we demonstrated that the structure of muzitone was misassigned.

引用

页码：5300 / 5308

页数：9

共 66 条

[1]

[Anonymous], [No title captured]

[2] ISOMERISM OF SOME ALPHA-HYDROXYSILANES TO SILYL ETHERS [J].