The synthesis of a 5,7-membered fused-ring compound by a tandem pummerer rearrangement and intramolecular [4+3] cycloaddition

被引:23
|
作者
Hu, YH [1 ]
Ou, LG [1 ]
Bai, DL [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Mat Med, Shanghai 200031, Peoples R China
关键词
D O I
10.1016/S0040-4039(98)02404-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A 5, 7-membered fused-ring compound with a functionalized angular substituent, 8-methoxy-8a alpha-methoxymethyl-7-phenylthio-1, 2, 3, 6-tehahydro-3a alpha, 6 beta-epoxyazulene, was synthesized via a tandem Pummerer rearrangement and intramolecular [4+3] cycloaddition. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:545 / 548
页数:4
相关论文
共 50 条
  • [1] Diastereoselective intramolecular [4+3] cycloaddition: Synthesis of a versatile precursor for preparation of 5,7-fused ring compounds
    Ou, LG
    Hu, YH
    Song, GQ
    Bai, DL
    [J]. TETRAHEDRON, 1999, 55 (49) : 13999 - 14004
  • [2] A Rapid and Stereocontrolled Synthesis of the Zizaane Ring System by Using an Intramolecular (4+3) Cycloaddition Reaction
    Laplace, Duchan R.
    Winne, Johan M.
    [J]. SYNLETT, 2015, 26 (04) : 467 - 470
  • [3] A Lewis acid catalyzed intramolecular [4+3] cycloaddition route to polycyclic systems that contain a seven-membered ring
    Prié, G
    Prévost, N
    Twin, H
    Fernandes, SA
    Hayes, JF
    Shipman, M
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (47) : 6517 - 6519
  • [4] Total synthesis of racemic lasidiol via intramolecular [4+3] cycloaddition
    Kreiselmeier, G
    Föhlisch, B
    [J]. TETRAHEDRON LETTERS, 2000, 41 (09) : 1375 - 1379
  • [5] SYNTHESIS OF FUSED-RING CYCLOBUTENONES VIA A TANDEM [2+2] CYCLOADDITION-BETA-ELIMINATION SEQUENCE
    GALATSIS, P
    ASHBOURNE, KJ
    MANWELL, JJ
    WENDLING, P
    DUFAULT, R
    HATT, KL
    FERGUSON, G
    GALLAGHER, JF
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (06): : 1491 - 1495
  • [6] Model Studies for the Preparation of Oxepanes and Fused Compounds by Tandem [4+3] Cycloaddition/Ring-Opening Metathesis/Cross Metathesis
    Disetti, Paolo
    Piras, Linda
    Moccia, Maria
    Saviano, Michele
    Adamo, Mauro F. A.
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (41) : 6202 - 6208
  • [7] Synthesis of the Tricyclic Ring Structure of Daphnanes via Intramolecular [4+3] Cycloaddition/SmI2-Pinacol Coupling
    Hassan, Ahmed H. E.
    Lee, Jae Kyun
    Pae, Ae Nim
    Min, Sun-Joon
    Cho, Yong Seo
    [J]. ORGANIC LETTERS, 2015, 17 (11) : 2672 - 2675
  • [8] Consecutive intramolecular azomethine ylid cycloaddition - Pummerer rearrangement as a strategy for the synthesis of enantiomerically pure 5-(hydroxymethyl)prolines
    Harwood, LM
    Lilley, IA
    [J]. SYNLETT, 1996, (10) : 1010 - &
  • [9] Formal enantioselective [4+3] cycloaddition by a tandem Diels-Alder reaction/ring expansion
    Dai, Xing
    Davies, Huw M. L.
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (16-17) : 2449 - 2456
  • [10] Synthesis of a 15-membered macrocyclic ketone and its transannular [4+3] cycloaddition reaction
    Conyers, Ryan C.
    Gung, Benjamin W.
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 238