A bioinspired, one-step total synthesis of peshawaraquinone

被引：4
|
作者：
de Castro, Tomas Vieira [1 ,2 ]
Huang, David M. M. [1 ]
Sumby, Christopher J. J. [1 ]
Lawrence, Andrew L. L. [2 ]
George, Jonathan H. H. [1 ]
机构：
[1] Univ Adelaide, Dept Chem, Adelaide, SA 5000, Australia
[2] Univ Edinburgh, EaStCHEM Sch Chem, Joseph Black Bldg,David Brewster Rd, Edinburgh EH9 3FJ, Scotland
来源：
CHEMICAL SCIENCE | 2023年 / 14卷 / 04期
基金：
澳大利亚研究理事会;
关键词：
ACID;
D O I：
10.1039/d2sc05377b
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A concise synthesis of a stereochemically complex meroterpenoid, peshawaraquinone, via the unsymmetrical dimerization of its achiral precursor, dehydro-alpha-lapachone, is reported. Enabled by reversible oxa-6 pi-electrocyclizations of 2H-pyran intermediates, the base-catalyzed dimerization sets up an intramolecular (3 + 2) cycloaddition, with the formation of six stereocenters during the cascade. Combining the generation and in situ dimerization of dehydro-alpha-lapachone allows a one-step total synthesis of peshawaraquinone from lawsone and prenal.
引用
收藏
页码：950 / 954
页数：5
相关论文
共 50 条
  • [11] Novel One-Step Total Synthesis of trans-Dehydroosthol and Citrubuntin
    Liu, Zhiwen
    Ge, Baoyue
    Gong, Xushun
    Wang, Fusheng
    Lei, Ting
    Jiang, Shizhi
    MOLECULES, 2025, 30 (05):
  • [12] Synthesis of pogostone by one-step
    Chen, Han-Bin
    Zhou, Jiang-Tao
    Liu, Yu-Hong
    Zhang, Zhen-Biao
    Zhan, Ya-Xian
    Su, Zi-Ren
    Zeng, Hui-Fang
    JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH, 2017, 19 (02) : 172 - 175
  • [13] ONE-STEP SYNTHESIS OF (+/-)-FRONTALIN
    KONGKATHIP, N
    KONGKATHIP, B
    JOURNAL OF THE SCIENCE SOCIETY OF THAILAND, 1992, 18 (04): : 225 - 227
  • [14] One-step synthesis of isocorroles
    Nardis, Sara
    Pomarico, Giuseppe
    Fronczek, Frank R.
    Vicente, Maria Graca H.
    Paolesse, Roberto
    TETRAHEDRON LETTERS, 2007, 48 (49) : 8643 - 8646
  • [15] One-Step Synthesis of Normoftal
    A. N. Balaev
    E. V. Reshetnikov
    V. E. Fedorov
    Pharmaceutical Chemistry Journal, 2014, 48 : 49 - 50
  • [16] One-Step Synthesis of Normoftal
    Balaev, A. N.
    Reshetnikov, E. V.
    Fedorov, V. E.
    PHARMACEUTICAL CHEMISTRY JOURNAL, 2014, 48 (01) : 49 - 50
  • [17] ONE-STEP SYNTHESIS OF DODECAMETHYLCYCLOHEXASILANE
    LAGUERRE, M
    DUNOGUES, J
    CALAS, R
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1978, (06) : 272 - 272
  • [18] A ONE-STEP SYNTHESIS OF DIHYDROFLAVONOLS
    MULCHANDANI, NB
    CHADHA, MS
    CHEMISTRY & INDUSTRY, 1964, (36) : 1554 - 1554
  • [19] One-step synthesis of diphenyhnethanes
    Wei, QY
    Luo, YG
    Zhou, M
    Tao, FY
    Zhang, GL
    SYNTHETIC COMMUNICATIONS, 2005, 35 (06) : 835 - 843
  • [20] ONE-STEP SYNTHESIS OF CYCLOPENTADIENYLCHLOROSILANES
    KOSHUTIN, VI
    MAKSIMOVA, LN
    EMYASHEV, VI
    SMIRNOV, VA
    ZHURNAL OBSHCHEI KHIMII, 1976, 46 (01): : 146 - 150
12345