Synthesis of Atromentin and Its O-Alkylated Natural Products

被引：11
|
作者：
Ye, Yue Qi [1 ,2 ]
Koshino, Hiroyuki [1 ]
Abe, Naoki [2 ]
Nakamura, Takemichi [1 ]
Hashizume, Daisuke [1 ]
Takahashi, Shunya [1 ]
机构：
[1] RIKEN, Wako, Saitama 3510198, Japan
[2] Tokyo Univ Agr, Fac Appl Biosci, Dept Nutr Sci, Setagaya Ku, Tokyo 1568502, Japan
来源：
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY | 2010年 / 74卷 / 11期
关键词：
terphenyl; atromentin; single-crystal X-ray analysis; Suzuki-Miyaura coupling; DERIVATIVES;
D O I：
10.1271/bbb.100451
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
The structure of a long-known natural pigment, atromentin, was established by a total synthesis based on double Suzuki-Miyaura coupling and by a single-crystal X-ray analysis of the synthetic sample thereby obtained. A similar strategy including ceric ammonium nitrate (CAN) oxidation was applied to prepare 2-O-methoxyatromentin and thelephantin I.
引用
收藏
页码：2342 / 2344
页数：3
相关论文
共 50 条
  • [41] ALKYLATION OF PHOSPHORUS KETO-YLIDS AND REARRANGEMENT OF O-ALKYLATED PHOSPHONIUM SALTS
    NEOMEYANOV, NA
    BERMAN, ST
    REUTOV, OA
    BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1975, 24 (12): : 2737 - 2737
  • [42] Preparation of soluble N and o-alkylated polyanilines using a chemical biphasic process
    Falcou, A.
    Longeau, A.
    Marsacq, D.
    Hourquebie, P.
    Duchene, A.
    Synthetic Metals, 1999, 101 (01): : 647 - 648
  • [43] Asymmetric synthesis of O-alkylated tetronic acid derivatives via an organocatalytic Mannich reaction and subsequent intramolecular cyclization
    Luo, Nian-hua
    Sun, Xiang
    Yan, Yun-yun
    Nie, Shao-zhen
    Yan, Ming
    TETRAHEDRON-ASYMMETRY, 2011, 22 (14-15) : 1536 - 1541
  • [44] Synthesis of regioisomeric N- and O-alkylated 3-polyfluoroalkyl-1,2-dihydroquinoxalin-2-ones
    A. E. Ivanova
    O. G. Khudina
    Ya. V. Burgart
    V. I. Saloutin
    Russian Chemical Bulletin, 2011, 60 : 937 - 941
  • [45] A STABLE O-ALKYLATED SULFONE - REACTIONS AND X-RAY CRYSTALLOGRAPHIC STRUCTURE
    RONGIONE, JC
    MARTIN, JC
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1990, 199 : 389 - ORGN
  • [46] Ozonolyses of O-alkylated ketoximes in the presence of carbonyl groups: A facile access to ozonides
    Griesbaum, K
    Liu, XJ
    Kassiaris, A
    Scherer, M
    LIEBIGS ANNALEN-RECUEIL, 1997, (07): : 1381 - 1390
  • [47] A HIGHLY SENSITIVE AND SPECIFIC METHOD FOR QUANTITATION OF O-ALKYLATED DNA ADDUCTS AND ITS APPLICATION TO THE ANALYSIS OF HUMAN TISSUE DNA
    KANG, HI
    KONISHI, C
    KUROKI, T
    HUH, NH
    ENVIRONMENTAL HEALTH PERSPECTIVES, 1993, 99 : 269 - 271
  • [48] Synthesis and biological evaluation of N- and O-alkylated bicyclic furanopyrimidines as non-nucleosidic inhibitors of human cytomegalovirus
    Kelleher, MR
    McGuigan, C
    Andrei, G
    Snoeck, R
    De Clercq, E
    Balzarini, J
    NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2005, 24 (5-7): : 639 - 641
  • [49] Solid-Phase Methodology for Synthesis of O-Alkylated Aromatic Oligoamide Inhibitors of α-Helix-Mediated ProteinProtein Interactions
    Murphy, Natasha S.
    Prabhakaran, Panchami
    Azzarito, Valeria
    Plante, Jeffrey P.
    Hardie, Michaele J.
    Kilner, Colin A.
    Warriner, Stuart L.
    Wilson, Andrew J.
    CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (18) : 5546 - 5550
  • [50] INHIBITORY EFFECT OF O-ALKYLATED ANALOGS OF OXYTOCIN AND VASOPRESSIN ON HUMAN AND RAT MYOMETRIAL ACTIVITY
    MELIN, P
    VILHARDT, H
    LINDEBERG, G
    LARSSON, LE
    AKERLUND, M
    JOURNAL OF ENDOCRINOLOGY, 1981, 88 (02) : 173 - 180
12345