FORMAL TOTAL SYNTHESIS OF XESTOQUINONE VIA FURAN RING TRANSFER-REACTION STRATEGY

被引:31
|
作者
KANEMATSU, K
SOEJIMA, S
WANG, GL
机构
[1] Institute of Synthetic Organic Chemistry, Faculty of Pharmaceutical Sciences, Kyushu University 62, Higashiku, Fukuoka, 812, Maidashi
关键词
XESTOQUINONE; FUSED FURAN; FURAN RING TRANSFER REACTION; CYCLOADDITION; FRIEDEL-CRAFTS ACYLATION;
D O I
10.1016/S0040-4039(00)92301-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A formal total synthesis of the marine natural product xestoquinone (5) based upon FRT reaction strategy is accomplished by preparation of the pentacyclic furan 6, an advanced key intermediate in Harada's previous total synthesis of this target
引用
收藏
页码:4761 / 4764
页数:4
相关论文
共 50 条
  • [1] TOTAL SYNTHESIS OF EURYFURAN VIA 2 SEQUENTIAL FURAN RING TRANSFER-REACTION
    KANEMATSU, K
    SOEJIMA, S
    HETEROCYCLES, 1991, 32 (08) : 1483 - 1486
  • [2] CHIRALITY TRANSFER FROM THE FURAN RING TRANSFER-REACTION
    YAMAGUCHI, Y
    TATSUTA, N
    HAYAKAWA, K
    KANEMATSU, K
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (08) : 470 - 472
  • [3] ALTERNATIVE SYNTHETIC APPROACHES TO (+/-)-EURYFURAN VIA THE FURAN RING TRANSFER-REACTION
    BABA, Y
    SAKAMOTO, T
    SOEJIMA, S
    KANEMATSU, K
    TETRAHEDRON, 1994, 50 (19) : 5645 - 5658
  • [4] Formal total synthesis of camptothecin via ring-closing metathesis strategy
    Chavan, SP
    Pasupathy, K
    Venkatraman, MS
    Kale, RR
    TETRAHEDRON LETTERS, 2004, 45 (37) : 6879 - 6882
  • [5] AN EFFICIENT CHIRALITY TRANSFER FROM THE FURAN RING TRANSFER-REACTION OF THE TETRAHYDROBENZOFURANYL ALLENYL ETHER FOLLOWED BY ANGULAR ALKYLATION VIA THE CLAISEN REARRANGEMENT
    KANEMATSU, K
    NISHIZAKI, A
    SATO, Y
    SHIRO, M
    TETRAHEDRON LETTERS, 1992, 33 (34) : 4967 - 4970
  • [6] CONVERSION OF AZIDOTRIAZOLINES TO TETRAZOLES VIA DIAZO TRANSFER-REACTION
    KADABA, PK
    HETEROCYCLES, 1984, 21 : 372 - 372
  • [7] AN EFFICIENT FURAN RING TRANSFER-REACTION - A VERSATILE KEY INTERMEDIATE LEADING TO THE BASIC SKELETON OF NATURALLY-OCCURRING FUSED FURANS
    YAMAGUCHI, Y
    HAYAKAWA, K
    KANEMATSU, K
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (07) : 515 - 516
  • [8] Formal Total Synthesis of (±)-Cephalotaxine and Congeners via Aryne Insertion Reaction
    Gouthami, Pashikanti
    Chegondi, Rambabu
    Chandrasekhar, Srivari
    ORGANIC LETTERS, 2016, 18 (09) : 2044 - 2046
  • [9] A formal total synthesis of (+/-)-gephyrotoxin via the intramolecular Schmidt reaction.
    Fang, WK
    Pearson, WH
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1997, 213 : 556 - ORGN
  • [10] Total Synthesis of (±)-Cafestol: A Late-Stage Construction of the Furan Ring Inspired by a Biosynthesis Strategy
    Zhu, Lili
    Luo, Jisheng
    Hong, Ran
    ORGANIC LETTERS, 2014, 16 (08) : 2162 - 2165