Total Synthesis of Rhodonoids A, B, E, and F, Enabled by Singlet Oxygen Ene Reactions

被引：17
|
作者：
Burchill, Laura [1 ]
George, Jonathan H. [1 ]
机构：
[1] Univ Adelaide, Dept Chem, Adelaide, SA 5005, Australia
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 04期
基金：
澳大利亚研究理事会;
关键词：
BIOMIMETIC TOTAL-SYNTHESIS; (+/-)-RHODONOIDS; PAIRS;
D O I：
10.1021/acs.joc.9b02968
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Singlet oxygen is a versatile reagent for the selective oxidation of organic compounds under mild reaction conditions. It is frequently invoked in biosynthetic pathways, so it is especially suitable for application in the biomimetic synthesis of natural products. Herein, we show that use of the singlet oxygen ene reaction, combined with [2 + 2] cycloadditions, leads to concise, divergent, and redox-economic total syntheses of several polycyclic members of the rhodonoid family of meroterpenoids.
引用
收藏
页码：2260 / 2265
页数：6
相关论文
共 50 条
  • [41] Total Synthesis of Dictyodendrins B and E
    Liang, Jingjing
    Hu, Weimin
    Tao, Pengyu
    Jia, Yanxing
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (11): : 5810 - 5815
  • [42] Stereoselective total synthesis of paecilomycins e and F
    Organic Chemistry Division-1, Indian Institute of Chemical Technology, Hyderabad
    500 007, India
    Synthesis, 10 (1499-1509):
  • [43] Stereoselective Total Synthesis of Paecilomycins E and F
    Bhunia, Nisith
    Das, Biswanath
    SYNTHESIS-STUTTGART, 2015, 47 (10): : 1499 - 1509
  • [44] PHOTOOXYGENATION OF TETRAMETHYLALLENE COMPETING (2+2) CYCLO-ADDITION AND ENE-REACTIONS WITH SINGLET OXYGEN
    GOLLNICK, K
    SCHNATTERER, A
    TETRAHEDRON LETTERS, 1985, 26 (41) : 5029 - 5032
  • [45] Quadruple 'ene' reactions of singlet oxygen to the natural product hyperforin: A computed study of polyhydroperoxides with decomposition to hydrotrioxide and carbonyls
    Olson, Jeff
    Abramova, Inna
    Rudshteyn, Benjamin
    Walalawela, Niluksha
    Greer, Alexander
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 252
  • [46] SELF-SENSITIZED ENE REACTIONS OF 1,9-(4-CYCLOHEXENO)BUCKMINSTERFULLERENES WITH SINGLET OXYGEN
    AN, YZ
    RUBIN, Y
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1995, 209 : 66 - ORGN
  • [47] Formal Total Synthesis of Batrachotoxin Enabled by Radical and Weix Coupling Reactions
    Watanabe, Yuuki
    Sakata, Komei
    Urabe, Daisuke
    Hagiwara, Koichi
    Inoue, Masayuki
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (24): : 17479 - 17484
  • [48] Study on the total synthesis of hainanolide (V) - Oxidation of the tricyclic alkenes with singlet oxygen
    Yu, XM
    Zhang, LY
    Chen, SZ
    Huang, L
    CHINESE CHEMICAL LETTERS, 1999, 10 (08) : 657 - 658
  • [49] Study on the Total Synthesis of Hainanolide (V)-Oxidation of the Tricyclic Alkenes with Singlet Oxygen
    Xiao Ming YU
    Lu Yan ZHANG
    Shi Zhi CHEN
    Liang HUANG (Institute of Materia Medica
    ChineseChemicalLetters, 1999, (08) : 657 - 658
  • [50] VICINAL TRICARBONYL PRODUCTS FROM SINGLET OXYGEN REACTIONS - APPLICATION TO THE SYNTHESIS OF CARBACEPHAMS
    WASSERMAN, HH
    HAN, WT
    TETRAHEDRON LETTERS, 1984, 25 (34) : 3743 - 3746
12345