Synthesis of the Tetracyclic ABCD Ring Systems of Madangamines D-F

被引:18
|
作者
Diaba, Faiza [1 ]
Pujol-Grau, Climent [1 ]
Martinez-Laporta, Agustin [1 ]
Fernandez, Israel [2 ]
Bonjoch, Josep [1 ]
机构
[1] Univ Barcelona, Fac Farm, IBUB, Lab Quim Organ, E-08028 Barcelona, Spain
[2] Univ Complutense Madrid, Fac Ciencias Quim, Dept Quim Inorgan 1, E-28040 Madrid, Spain
关键词
1ST ENANTIOSELECTIVE SYNTHESIS; DIAZATRICYCLIC CORE; RADICAL CYCLIZATION; CLOSING METATHESIS; MARINE ALKALOIDS; CONCISE APPROACH; TRICYCLIC CORE; STEREOCHEMISTRY; ALKENES; ROUTE;
D O I
10.1021/ol503586d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Synthesis of the tetracyclic cores of madangamines D-F was achieved, featuring a reductive radical process from an ethoxycarbonyldichloroacetamide to build the morphan nucleus, a Mitsunobu-type aminocyclization toward the common diazatricyclic intermediate, and ring-closing metathesis reactions for the macrocyclization step leading to the 13- to 15-membered rings.
引用
收藏
页码:568 / 571
页数:4
相关论文
共 50 条
  • [21] Application of Chlorosulfonyl Isocyanate (CSI) in the Synthesis of Fused Tetracyclic Ketone Ring Systems
    VanNatta, Jennifer M.
    Niu, Haichan
    Carlson, Graham J.
    Pinney, Kevin G.
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (21): : 15636 - 15651
  • [22] ON TRIAZOLES .7. SYNTHESIS OF NOVEL TRICYCLIC AND TETRACYCLIC RING-SYSTEMS
    REITER, J
    PONGO, L
    KRAJCSI, P
    ESSESREITER, K
    SOHAR, P
    MOLNAR, H
    DVORTSAK, P
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1987, 24 (04) : 927 - 930
  • [23] UNIFIED TREATMENT OF C-F MIXING AND D-F COULOMB INTERACTION IN F-ELECTRON SYSTEMS
    KASUYA, T
    SAKAI, O
    TAKEGAHARA, K
    TAKESHIGE, M
    JOURNAL OF MAGNETISM AND MAGNETIC MATERIALS, 1985, 52 (1-4) : 1 - 6
  • [24] FORMULATION OF THE D-F INTERACTION IN FERROMAGNETIC SUPERCONDUCTORS
    MATSUMOTO, H
    UMEZAWA, H
    WHITEHEAD, JP
    PHYSICAL REVIEW B, 1984, 30 (03): : 1294 - 1313
  • [25] Periodic Anderson Model with d-f Interaction
    Hagymasi, I.
    Itai, K.
    Solyom, J.
    ACTA PHYSICA POLONICA A, 2012, 121 (5-6) : 1070 - 1072
  • [26] THE FIRST SYNTHESIS OF THE ABCD RING-SYSTEM OF MANZAMINE-A - CONSTRUCTION OF THE MACROCYCLIC RING-D
    BORER, BC
    DEERENBERG, S
    BIERAUGEL, H
    PANDIT, UK
    TETRAHEDRON LETTERS, 1994, 35 (19) : 3191 - 3194
  • [27] Synthesis of d-f coordination polymer nanoparticles and their application in phosphorescence and magnetic resonance imaging
    Zhou, Zhiguo
    Li, Darui
    Yang, Hong
    Zhu, Yachao
    Yang, Shiping
    DALTON TRANSACTIONS, 2011, 40 (44) : 11941 - 11944
  • [28] Synthesis and crystal structure of d-f heteronuclear Gd(III)-Co(II) system
    Wu, Bin
    JOURNAL OF COORDINATION CHEMISTRY, 2008, 61 (16) : 2558 - 2562
  • [29] Diastereoselective Synthesis of Cyclopentanoids: Applications to the Construction of the ABCD Tetracyclic Core of Retigeranic Acid A
    Zhang, Junlin
    Wang, Xiao
    Li, Shuang
    Li, Dian
    Liu, Song
    Lan, Yu
    Gong, Jianxian
    Yang, Zhen
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (36) : 12596 - 12600
  • [30] The broadening of d-f and f-d transitions by collisions with neutral hydrogen atoms
    Barklem, PS
    O'Mara, BJ
    Ross, JE
    MONTHLY NOTICES OF THE ROYAL ASTRONOMICAL SOCIETY, 1998, 296 (04) : 1057 - 1060