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
  • [31] Divergent synthesis of the tetracyclic ethers of 6-X-7-6 ring systems
    Inoue, M
    Wang, J
    Wang, GX
    Ogasawara, Y
    Hirama, M
    TETRAHEDRON, 2003, 59 (30) : 5645 - 5659
  • [32] Synthesis of tetracyclic indole-containing ring systems by intramolecular cycloadditions of azomethine ylides
    Coldham, Iain
    Dobson, Benjamin C.
    Franklin, Andrew I.
    Fletcher, Stephen R.
    TETRAHEDRON LETTERS, 2007, 48 (05) : 873 - 875
  • [33] Stereoselective synthesis of the ABCD ring framework of azaspiracids
    Yadav, J. S.
    Joyasawal, Sipak
    Dutta, S. K.
    Kunwar, A. C.
    TETRAHEDRON LETTERS, 2007, 48 (30) : 5335 - 5340
  • [34] Synthetic studies of kampanols, novel p21ras farnesyltransferase inhibitors:: an efficient synthesis of the tetracyclic ABCD ring system of kampanols
    Iwasaki, K
    Nakatani, M
    Inoue, M
    Katoh, T
    TETRAHEDRON, 2003, 59 (44) : 8763 - 8773
  • [35] EFFECTS OF D-F CORRELATION ON THE MIXED-VALENCE PROPERTIES OF CERIUM SYSTEMS - THE F-BAND PROBLEM
    LIU, SH
    HO, KM
    PHYSICAL REVIEW B, 1984, 30 (06): : 3039 - 3046
  • [36] ORGN 749-Synthesis of the eleven-membered ring of the marine alkaloids, madangamines
    Yamazaki, Naoki
    Yoshimura, Yuta
    Inoue, Junji
    Aoyagi, Sakae
    Kibayashi, Chihiro
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 232
  • [37] Synthesis and crystal structure of the first d-f heterodinuclear Dy(III)-Cu(II) cryptate
    Chen, QY
    Luo, QH
    Wang, ZL
    Chen, JT
    CHEMICAL COMMUNICATIONS, 2000, (12) : 1033 - 1034
  • [38] STUDY OF D-F HYBRIDIZATION IN ACTINIDE METALS AND ALLOYS
    JULLIEN, R
    COQBLIN, B
    PHYSICAL REVIEW B, 1973, 8 (11): : 5263 - 5271
  • [39] RENAISSANCE LATIN ARISTOTLE COMMENTARIES - AUTHORS D-F
    LOHR, CH
    RENAISSANCE QUARTERLY, 1976, 29 (04) : 714 - 745
  • [40] Cytotoxic Dibohemamines D-F from a Streptomyces Species
    Jiang, Bingya
    Zhao, Wei
    Li, Shufen
    Liu, Hongyu
    Yu, Liyan
    Zhang, Yixuan
    He, Hongwei
    Wu, Linzhuan
    JOURNAL OF NATURAL PRODUCTS, 2017, 80 (10): : 2825 - 2829