A NOVEL-APPROACH TO THE ASYMMETRIC-SYNTHESIS OF MANZAMINE-A - CONSTRUCTION OF THE TETRACYCLIC ABCE RING-SYSTEM

被引:107
|
作者
MARTIN, SF
LIAO, YS
WONG, YL
REIN, T
机构
[1] Department of Chemistry and Biochemistry, The University of Texas, Austin
关键词
D O I
10.1016/S0040-4039(00)75792-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The enantiomerically pure tetracyclic ABCE subunit of manzamine A has been constructed by an intramolecular Diels-Alder reaction of the vinylogous imide 13 to give the ABC tricyclic core 14; elaboration of 14 into 16 followed by a novel olefin metathesis reaction to form the azocine ring then delivered the tetracycle 17.
引用
收藏
页码:691 / 694
页数:4
相关论文
共 50 条
  • [21] Synthesis and Evaluation of the Tetracyclic Ring-System of Isocryptolepine and Regioisomers for Antimalarial, Antiproliferative and Antimicrobial Activities
    Haheim, Katja S.
    Lindback, Emil
    Tan, Kah Ni
    Albrigtsen, Marte
    Urdal Helgeland, Ida T.
    Lauga, Clemence
    Matringe, Theodora
    Kennedy, Emily K.
    Andersen, Jeanette H.
    Avery, Vicky M.
    Sydnes, Magne O.
    MOLECULES, 2021, 26 (11):
  • [22] SYNTHESIS OF SUBSTITUTED BENZOPHENALENOFURANS - NOVEL PENTACYCLIC RING-SYSTEM
    BRENNER, M
    BRUSH, C
    TETRAHEDRON LETTERS, 1977, (05) : 419 - 422
  • [23] SYNTHESIS OF 2 NOVEL PYRIDAZINES - NEW RING-SYSTEM
    COPPOLA, GM
    GIMELLI, SP
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1973, 10 (03) : 323 - 324
  • [24] NOVEL SYNTHESIS OF THE BENZO[F]QUINAZOLINE RING-SYSTEM
    DELIA, TJ
    MUNSLOW, WD
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1979, 16 (02) : 239 - 240
  • [25] NOVEL-APPROACH TO THE ASYMMETRIC-SYNTHESIS OF PEPTIDE-FRAGMENTS BEARING ALPHA-HYDORXY-BETA-AMINO ACID RESIDUES
    OJIMA, I
    ZHAO, M
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1991, 202 : 48 - ORGN
  • [26] TOTAL SYNTHESIS OF TETRACYCLIC TRITERPENES .1. THE (+/-)-5-EPI-EUPHANE RING-SYSTEM
    KOLACZKOWSKI, L
    REUSCH, W
    JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (24): : 4766 - 4771
  • [27] STEREOSPECIFIC SYNTHESIS OF THE CYCLOPENTA[E]PHENANTHRIDINE RING-SYSTEM - TETRACYCLIC AND PENTACYCLIC ANALOGS OF CEPHALOTAXUS ALKALOIDS
    BRYCE, MR
    GARDINER, JM
    TETRAHEDRON, 1988, 44 (02) : 599 - 612
  • [28] A NOVEL-APPROACH TO THE SYNTHESIS OF MEDIUM RING NITROGEN-HETEROCYCLES
    SHAW, R
    ANDERSON, M
    GALLAGHER, T
    SYNLETT, 1990, (10) : 584 - 586
  • [29] NOVEL CONSTRUCTION OF QUINOLINE RING-SYSTEM BY ELECTROCYCLIC REACTION OF AZAHEXATRIENE DERIVATIVES
    KAMETANI, T
    SUZUKI, Y
    TAKEDA, H
    KASAI, H
    YAMAZAKI, K
    TAKADA, N
    HONDA, T
    YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 1987, 107 (02): : 107 - 110
  • [30] 2ND APPROACH TO THE CONSTRUCTION OF A PENTACYCLIC RING-SYSTEM FOR NEOSURUGATOXIN
    OKADA, K
    MIZUNO, Y
    TANINO, H
    KAKOI, H
    INOUE, S
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1992, 40 (05) : 1110 - 1115