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
  • [41] RADIOFREQUENCY RESONANCE MEASUREMENTS OF NA D-F INTERVALS
    TRAN, NH
    VANDENHEUVELL, HBV
    KACHRU, R
    GALLAGHER, TF
    PHYSICAL REVIEW A, 1984, 30 (04) : 2097 - 2099
  • [42] Synthesis of a new tetracyclic ring system: pyrrolotriazepinoquinazolinone derivatives
    Foeldesi, Tamas
    Dancso, Andras
    Simig, Gyula
    Volk, Balazs
    Milen, Matyas
    TETRAHEDRON, 2015, 71 (38) : 6759 - 6763
  • [43] Synthesis of some tricyclic and tetracyclic ring systems built on 4-hydroxy-2-quinolones
    Dodia, N
    Shah, A
    HETEROCYCLIC COMMUNICATIONS, 2001, 7 (03) : 289 - 294
  • [44] A Concise Approach for the Synthesis of the ABCD Ring System of Alpkinidine
    Volvoikar, Prajesh S.
    Tilve, Santosh G.
    Zubkov, Fedor, I
    CHEMISTRYSELECT, 2019, 4 (24): : 7187 - 7189
  • [45] REGIOSELECTIVE SYNTHESIS OF THE KINAMYCIN ABCD RING-SYSTEM
    OSULLIVAN, PJ
    MORENO, R
    MURPHY, WS
    TETRAHEDRON LETTERS, 1992, 33 (04) : 535 - 538
  • [46] Diastereoselective Synthesis of the ABCD Ring System of Rubriflordilactone B
    Roth, Hudson G.
    Nicewicz, David A.
    SYNLETT, 2022, 33 (01) : 48 - 51
  • [47] Synthesis and Biological Evaluation of ABCD Ring Fragments of the Kibdelones
    Sloman, David L.
    Mitasev, Branko
    Scully, Stephen S.
    Beutler, John A.
    Porco, John A., Jr.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (11) : 2511 - 2515
  • [48] Synthesis of the polycyclic ring systems of artocarpol A and D
    Paduraru, MP
    Wilson, PD
    ORGANIC LETTERS, 2003, 5 (25) : 4911 - 4913
  • [49] Sensitised luminescence in lanthanide containing arrays and d-f hybrids
    Faulkner, Stephen
    Natrajan, Louise S.
    Perry, William S.
    Sykes, Daniel
    DALTON TRANSACTIONS, 2009, (20) : 3890 - 3899
  • [50] Novel d-f bimetallic complexes containing macrocyclic ligand
    Yuen, Pong
    Lau, Cheng Man Diana
    Yuen, Aaron K.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 257