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.

引用

页码：1485 / 1490

页数：6

共 50 条

[41] Synthesis of Biaryl Compounds Using Tandem Ruthenium-Catalyzed Ring-Closing Metathesis
Yoshida, Kazuhiro
Shida, Hiroaki
Takahashi, Hidetoshi
Yanagisawa, Akira
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (01) : 344 - 349
[42] An efficient synthesis of trihydroxy quinolizidine alkaloids using ring-closing metathesis
Dhavale, DD
Jachak, SM
Karche, NP
Trombini, C
SYNLETT, 2004, (09) : 1549 - 1552
[43] Cross-metathesis and ring-closing metathesis of olefinic monosaccharides
Postema, MHD
Piper, JL
TETRAHEDRON LETTERS, 2002, 43 (39) : 7095 - 7099
[44] Dienyne ring-closing metathesis approach for the construction of taxosteroids
Aldegunde, Maria J.
Garcia-Fandino, Rebeca
Castedo, Luis
Granja, Juan R.
CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (18) : 5135 - 5150
[45] Enantioconservative synthesis and ring closing metathesis of disubstituted dialkenic amides
Sauriat-Dorizon, H
Guibé, F
TETRAHEDRON LETTERS, 1998, 39 (37) : 6711 - 6714
[46] Ring-closing olefin metathesis for the synthesis of benzene derivatives
Yoshida, Kazuhiro
Kawagoe, Fumihiro
Iwadate, Noriyuki
Takahashi, Hidetoshi
Imamoto, Tsuneo
CHEMISTRY-AN ASIAN JOURNAL, 2006, 1 (04) : 611 - 613
[47] Synthesis of heterocycles containing an N-O bond by ring-closing metathesis of dienes tethered by hydroxylamine
Yang, YK
Tae, J
SYNLETT, 2003, (07) : 1043 - 1045
[48] Synthesis of substituted pyridines and pyridazines via ring closing metathesis
Donohoe, Timothy J.
Fishlock, Lisa P.
Basutto, Jose A.
Bower, John F.
Procopiou, Panayiotis A.
Thompson, Amber L.
CHEMICAL COMMUNICATIONS, 2009, (21) : 3008 - 3010
[49] Multiple Olefin Metathesis Polymerization That Combines All Three Olefin Metathesis Transformations: Ring-Opening, Ring-Closing, and Cross Metathesis
Lee, Ho-Keun
Bang, Ki-Taek
Hess, Andreas
Grubbs, Robert H.
Choi, Tae-Lim
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (29) : 9262 - 9265
[50] Synthesis of β-bisabolol by ring-closing olefin metathesis reaction
Spitzner, D
Zepf, J
NATURAL PRODUCT RESEARCH, 2006, 20 (01) : 99 - 102

← 1 2 3 4 5 →