Synthesis of Acyloxy-Semicyclic Dienes Using an Enyne Metathesis/Ring Closing Metathesis Approach

被引：2

作者：

Kueh, Jui Thiang Brian ^{[1
]}

Moodie, Lindon W. K. ^{[2
]}

Lucas, Nigel T. ^{[1
]}

Larsen, David S. ^{[1
]}

机构：

[1] Univ Otago, Dept Chem, Dunedin, New Zealand

[2] Univ Tromso, Dept Chem, N-9037 Tromso, Norway

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 2015卷 / 07期

关键词：

Synthetic methods; Metathesis; Cycloaddition; Enynes; Vinyl esters; RING-OPENING/CROSS-METATHESIS; ANGUCYCLINE ANTIBIOTICS; CROSS-METATHESIS; SELECTIVITY; REACTIVITY; DERIVATIVES;

D O I：

10.1002/ejoc.201403482

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An enyne metathesis/ring closing metathesis (EM/RCM) sequence was used to synthesise acyloxy-semicyclic dienes from an enyne substrate and various vinyl esters. This allowed convenient access to acyloxy-semicyclic dienes not accessible by cross metathesis alone due to the low reactivity of Fischer carbenes with the termini of 1,3-dienes. This new approach also provides an alternative method for the synthesis of 1-acyloxy-1,3-dienes which are useful reactants for Diels-Alder cycloadditions.

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页码：1485 / 1490

页数：6

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