Comparison of approaches to ent-morphine via radical, cationic, and Heck-type cyclizations

被引：12

作者：

Frey, DA ^{[1
]}

Duan, CM ^{[1
]}

Ghiviriga, I ^{[1
]}

Hudlicky, T ^{[1
]}

机构：

[1] Univ Florida, Dept Chem, Gainesville, FL 32611 USA

来源：

COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS | 2000年 / 65卷 / 04期

关键词：

morphine; Heck reaction; alkaloids; biooxidation; total synthesis; palladium; cascade cyclizations;

D O I：

10.1135/cccc20000561

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

3-(2-{6S-(2-Bromo-6-methoxyphenoxy)-5S-[tert-butyl(dimethyl)silyloxy)cyclohex-1-en-1-yl}-ethyl)oxazol-2(3H)-one 14 was subjected to Heck cyclization conditions to afford dibenzofuran derivative 16. The comparison of stepwise vs cascade approaches to 8 via radical, cationic, and Heck-type cyclizations is discussed.

引用

页码：561 / 569

页数：9

共 28 条

[1] Intramolecular N-acyliminium ion-olefin cyclization in the synthesis of optically pure isoquinoline derivatives: Control of stereochemistry and application to synthesis of morphine alkaloids [J].