Chemical synthesis of the GHIJKLMNO ring system of maitotoxin

被引:0
|
作者
Nicolaou, K.C.
Frederick, Michael O.
Burtoloso, Antonio C. B.
Denton, Ross M.
Rivas, Fatima
Cole, Kevin P.
Aversa, Robert J.
Gibe, Romelo
Umezawa, Taiki
Suzuki, Takahiro
机构
来源
Journal of the American Chemical Society | 2008年 / 130卷 / 23期
关键词
As the largest secondary metabolite to be discovered as of yet; the polyether marine neurotoxin maitotoxin constitutes a major structural and synthetic challenge. After its originally proposed structure (1) had been questioned on the basis of biosynthetic considerations; we provided computational and experimental support for structure 1. In an effort to provide stronger experimental evidence: of the molecular architecture of maitotoxin; its GHIJKLMNO ring system 3 was synthesized. The 13C NMR chemical shifts of synthetic 3 matched closely those corresponding to the same domain of the natural product providing strong evidence for the correctness of the originally proposed structure of maitotoxin (1). © 2008 American Chemical Society;
D O I
暂无
中图分类号
学科分类号
摘要
Journal article (JA)
引用
收藏
页码:7466 / 7476
相关论文
共 50 条
  • [21] "Ring Breaker": Neural Network Driven Synthesis Prediction of the Ring System Chemical Space
    Thakkar, Amol
    Selmi, Nidhal
    Reymond, Jean-Louis
    Engkvist, Ola
    Bjerrum, Esben Jannik
    JOURNAL OF MEDICINAL CHEMISTRY, 2020, 63 (16) : 8791 - 8808
  • [22] Synthetic studies on maitotoxin.: 1.: Stereoselective synthesis of the C′D′E′F′-ring system having a side chain
    Morita, Masayuki
    Ishiyama, Seishi
    Koshino, Hiroyuki
    Nakata, Tadashi
    ORGANIC LETTERS, 2008, 10 (09) : 1675 - 1678
  • [23] SYNTHETIC STUDY OF THE C'D'E' RING SYSTEM OF MAITOTOXIN VIA FURAN BASED STRATEGY
    Watanabe, Yuta
    Torikai, Kohei
    Yasuno, Yoko
    Oishi, Tohru
    HETEROCYCLES, 2021, 102 (12) : 2313 - 2318
  • [24] Convergent Syntheses of the WXYZ Ring of Maitotoxin and the HIJK Ring of Brevisulcenal-F
    Osato, Naoya
    Onoue, Hisaaki
    Toma, Yoshiki
    Torikai, Kohei
    Ebine, Makoto
    Satake, Masayuki
    Oishi, Tohru
    CHEMISTRY LETTERS, 2018, 47 (03) : 265 - 268
  • [25] SYNTHESIS AND STEREOCHEMICAL CONFIRMATION OF THE CIS-FUSED L/M AND N/O RING-SYSTEMS OF MAITOTOXIN
    SASAKI, M
    NONOMURA, T
    MURATA, M
    TACHIBANA, K
    TETRAHEDRON LETTERS, 1994, 35 (28) : 5023 - 5026
  • [26] Rearrangement-ring expansion reaction of functionalized cyclic ethers. Stereoselective synthesis of the ST- and XY-ring systems of maitotoxin
    Nagasawa, K
    Hori, N
    Shiba, R
    NAkata, T
    HETEROCYCLES, 1997, 44 : 105 - 110
  • [27] Synthesis and biological evaluation of QRSTUVWXYZA′ domains of maitotoxin
    Nicolaou, K.C., 1600, American Chemical Society (136):
  • [28] Synthesis and Biological Evaluation of QRSTUVWXYZA′ Domains of Maitotoxin
    Nicolaou, K. C.
    Heretsch, Philipp
    Nakamura, Tsuyoshi
    Rudo, Anna
    Murata, Michio
    Konoki, Keiichi
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (46) : 16444 - 16451
  • [29] Synthesis of the trinervitane ring system
    Dauben, WG
    Lorenz, KL
    Dean, DW
    Shapiro, G
    Farkas, I
    TETRAHEDRON LETTERS, 1998, 39 (39) : 7079 - 7082
  • [30] A synthesis of the ring system of terpestacin
    Mermet-Mouttet, MP
    Gabriel, K
    Heissler, D
    TETRAHEDRON LETTERS, 1999, 40 (05) : 843 - 846