Diastereoselective synthesis of functionalised carbazoles via a sequential Diels-Alder/ene reaction strategy

被引：26

作者：

Cowell, Joseph ^{[1
]}

Abualnaja, Matokah ^{[1
]}

Morton, Stephanie ^{[1
]}

Linder, Ruth ^{[1
]}

Buckingham, Faye ^{[1
]}

Waddell, Paul G. ^{[1
]}

Probert, Michael R. ^{[1
]}

Hall, Michael J. ^{[1
]}

机构：

[1] Newcastle Univ, Sch Chem, Newcastle Upon Tyne NE1 7RU, Tyne & Wear, England

来源：

RSC ADVANCES | 2015年 / 5卷 / 21期

基金：

英国工程与自然科学研究理事会;

关键词：

VITRO ANTIPROLIFERATIVE ACTIVITIES; ENE REACTION; DOMINO REACTIONS; 3-VINYLINDOLES; CARBODIENOPHILES; 2-VINYLINDOLES; STAUROSPORINE; VINYLINDENES; ALKALOIDS; ANALOGS;

D O I：

10.1039/c5ra00499c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An operationally simple one-pot, three-component, diastereoselective synthesis of saturated carbazoles and related pyridazino[3,4-b] indoles, based on two sequential intermolecular pericyclic reactions, is described. The reaction sequence involves an intermolecular Diels-Alder (D-A) reaction of a 3-vinyl-1H-indole, containing an electron withdrawing N-protecting group, with a suitable dienophile. Due to the electron withdrawing nature of the N-protecting group the resultant D-A cycloadducts are sufficiently stabilised to allow for a subsequent in situ diastereospecific intermolecular ene reaction to take place with an added enophile, generating functionalised carbazoles with relative stereocontrol of up to four stereocentres.

引用

页码：16125 / 16152

页数：28

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