Dienyne ring-closing metathesis approach for the construction of taxosteroids

被引：22

作者：

Aldegunde, Maria J.

Garcia-Fandino, Rebeca

Castedo, Luis

Granja, Juan R. ^{[1
]}

机构：

[1] Univ Santiago, Dept Quim Organ, Santiago De Compostela 15782, Spain

[2] Univ Santiago, Fac Quim, Unidade Asociada, CSIC, Santiago De Compostela 15782, Spain

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2007年 / 13卷 / 18期

关键词：

medium-ring compounds; metathesis; ring-closing dienyne metathesis (RCDEYM); steroid analogues; taxosteroids;

D O I：

10.1002/chem.200601685

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A cascade dienyne ring-closing metathesis approach has been applied to the synthesis of the tetracyclic carbon framework of a new class of hybrid compounds-the taxosteroids-possessing carbon frameworks incorporating moieties characteristic of both taxanes (such as AB rings) and steroids (i.e., CD system and side chain). This tandem cyclization is highly stereoselective, allowing the one-step formation of the bicyclo[5.3.1]undecene system characteristic of taxol. In this work we describe the scope and limitations of such cyclizations.

引用

页码：5135 / 5150

页数：16

共 103 条

[1] Mechanistic studies of olefin metathesis by ruthenium carbene complexes using electrospray ionization tandem mass spectrometry [J].