Synthesis of eight-membered ring compounds using enyne metathesis

被引:83
|
作者
Mori, M [1 ]
Kitamura, T [1 ]
Sakakibara, N [1 ]
Sato, Y [1 ]
机构
[1] Hokkaido Univ, Grad Sch Pharmaceut Sci, Sapporo, Hokkaido 0600812, Japan
关键词
D O I
10.1021/ol991398a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] A novel procedure for synthesizing eight-membered ring compounds was developed using ruthenium-catalyzed enyne metathesis. When a CH2Cl2 solution Of enyne connected with catechol, o-amino phenol, or o-phenylenediamine was stirred in the presence of benzylidene ruthenium carbene complex (10 mol %) at room temperature overnight, an eight-membered ring compound was obtained in high yield. In a similar manner, monocyclic 1,4-diaza or 1-oxa-4-azacyclooctene derivative was obtained in high yield.
引用
收藏
页码:543 / 545
页数:3
相关论文
共 50 条
  • [21] Synthesis of eight-membered aminocyclitol analogues
    Zozik, Yunus
    Salamci, Emine
    Kilic, Ayse
    TETRAHEDRON LETTERS, 2017, 58 (52) : 4822 - 4826
  • [22] A formal asymmetric synthesis of (+)-anatoxin-a using an enantioselective deprotonation strategy on an eight-membered ring
    Aggarwal, VK
    Humphries, PS
    Fenwick, A
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1999, 38 (13-14) : 1985 - 1986
  • [23] Ring synthesis by tandem enyne metathesis
    Diver, Steven T.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 231
  • [24] PREPARATION OF SIX-MEMBERED AND EIGHT-MEMBERED RING DIMERS OF BUTADIENE
    HILLYER, JC
    SMITH, JV
    INDUSTRIAL AND ENGINEERING CHEMISTRY, 1953, 45 (05): : 1133 - 1136
  • [25] A ring-closing metathesis approach to eight-membered benzannelated scaffolds and subsequent internal alkene isomerizations
    Taher, Abu
    Aderibigbe, Blessing A.
    Morgans, Garreth L.
    Madeley, Lee G.
    Khanye, Setshaba D.
    van der Westhuizen, Leandi
    Fernandes, Manuel A.
    Smith, Vincent J.
    Michael, Joseph P.
    Green, Ivan R.
    van Otterlo, Willem A. L.
    TETRAHEDRON, 2013, 69 (08) : 2038 - 2047
  • [26] Origin of the selectivity in the ring-closing metathesis step of the synthesis of (-)-callyspongiolide: Formation of fourteen-versus eight-membered rings
    Diaz-Ruiz, Marina
    Urbina, Aina
    Llor, Nuria
    Bosch, Joan
    Amat, Mercedes
    Maseras, Feliu
    TETRAHEDRON, 2022, 124
  • [27] Medium ring stereocontrol in the functionalisation of eight-membered lactones
    Anderson, EA
    Holmes, AB
    Collins, I
    TETRAHEDRON LETTERS, 2000, 41 (01) : 117 - 121
  • [28] Synthesis of seven- and eight-membered carbasugar analogs via ring-closing metathesis and their inhibitory activities toward glycosidases
    Blériot, Y
    Giroult, A
    Mallet, JM
    Rodriguez, E
    Vogel, P
    Sinay, P
    TETRAHEDRON-ASYMMETRY, 2002, 13 (23) : 2553 - 2565
  • [29] How an Eight-Membered Ring Alters the Rhodamine Chromophore
    Poronik, Yevgen M.
    Ambicki, Filip
    Tseng, Sheng-Ming
    Chou, Pi-Tai
    Deperasinska, Irena
    Gryko, Daniel T.
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (09): : 5973 - 5980
  • [30] Rhodium-catalyzed [4+2+2] cycloaddition reactions for the synthesis of eight-membered ring compounds
    Canlas, Gino Martin R.
    Gilbertson, Scott R.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243