Ring-closing metathesis in the synthesis of large and medium-sized oxacycles.: Application to the synthesis of polyoxygenated macrocycles

被引：89

作者：

Delgado, M ^{[1
]}

Martín, JD ^{[1
]}

机构：

[1] CSIC, Inst Invest Quim, Ctr Invest Cient Isla La Cartuja, Seville 41092, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1999年 / 64卷 / 13期

关键词：

D O I：

10.1021/jo9901438

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ring-closing olefin metathesis (RCM) catalyzed by Grubbs's ruthenium benzylidene complex 1 is applied to the synthesis of unsaturated rings ranging in size from seven to thirteen members in trans-fused polyether systems. Reaction occurs with great efficiency in the cyclization of oxepene and oxocene rings, but as ring size increases, yields drop. The influence of the final double bond position is also studied. Better yields and milder reaction conditions are observed when an additional oxygen atom is introduced on the diene. This feature has promoted the application of this reaction to the synthesis of polyoxygenated macrocycles (with sizes ranging from 15 to 21 members), with excellent results.

引用

页码：4798 / 4816

页数：19

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