A facile and highly atom-economic approach to biaryl-containing medium-ring bislactones

被引:18
作者
Wu, Dongdong [1 ]
Wang, Lei [1 ]
Xu, Kai [1 ]
Song, Jia [1 ]
Fun, Hoong-Kun [2 ]
Xu, Jianhua [1 ]
Zhang, Yan [1 ]
机构
[1] Nanjing Univ, Sch Chem & Chem Engn, State Key Lab Analyt Chem Life Sci, Nanjing 210093, Jiangsu, Peoples R China
[2] Univ Sains Malaysia, Sch Phys, Xray Crystallog Unit, Usm Penang 11800, Malaysia
基金
中国国家自然科学基金;
关键词
SINGLET OXYGEN; ORGANOCUPRATE OXIDATION; NATURAL-PRODUCTS; O-QUINONES; PHOTOOXYGENATION; CHEMISTRY; SYSTEMS; REGIO;
D O I
10.1039/c2cc16492b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Starting from readily available phenanthrenequinone and alkenes, biaryl containing medium-ring bislactones could be easily prepared through sequential photocycloaddition-photooxidation reactions with good yields and diastereoselectivity.
引用
收藏
页码:1168 / 1170
页数:3
相关论文
共 35 条
  • [1] [Anonymous], 1995, ACTIVE OXYGEN CHEM
  • [2] Photochemical Reactions as Key Steps in Natural Product Synthesis
    Bach, Thorsten
    Hehn, Joerg P.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (05) : 1000 - 1045
  • [3] Electron transfer and singlet oxygen mechanisms in the photooxygenation of dibutyl sulfide and thioanisole in MeCN sensitized by N-methylquinolinium tetrafluoborate and 9,10-dicyanoanthracene.: The probable involvement of a thiadioxirane intermediate in electron transfer photooxygenations
    Baciocchi, E
    Del Giacco, T
    Elisei, F
    Gerini, MF
    Guerra, M
    Lapi, A
    Liberali, P
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (52) : 16444 - 16454
  • [4] Boye O., 1992, ALKALOIDS, V41, P125
  • [5] Atroposelective Total Synthesis of Axially Chiral Biaryl Natural Products
    Bringmann, Gerhard
    Gulder, Tanja
    Gulder, Tobias A. M.
    Breuning, Matthias
    [J]. CHEMICAL REVIEWS, 2011, 111 (02) : 563 - 639
  • [6] Chemistry of trans-Resveratrol with Singlet Oxygen: [2+2] Addition, [4+2] Addition, and Formation of the Phytoalexin Moracin M
    Celaje, Jeff A.
    Zhang, Dong
    Guerrero, Angela M.
    Selke, Matthias
    [J]. ORGANIC LETTERS, 2011, 13 (18) : 4846 - 4849
  • [7] SENSITIZED PHOTOOXYGENATION .1. REACTION OF SINGLET OXYGEN WITH 3,4-DIHYDRO-6-METHYL-2H-PYRAN-5-CARBOXYLIC ACID ETHYL-ESTER - ISOLATION OF HYDROPEROXIDES AND EVIDENCE OF THE TRANSFORMATION OF ONE OF THEM TO DIOXETANE
    CHAN, YY
    ZHU, C
    LEUNG, HK
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (18) : 5274 - 5275
  • [8] Photoaddition reactions of 1,2-diketones with silyl ketene acetals.: Formation of β-hydroxy-γ-ketoesters
    Cho, Dae Won
    Lee, Hyang-Yeol
    Oh, Sun Wha
    Choi, Jung Hei
    Park, Hea Jung
    Mariano, Patrick S.
    Yoon, Ung Chan
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (12) : 4539 - 4547
  • [9] MECHANISM OF PHENANTHRENEQUINONE PHOTOCYCLOADDITION TO OLEFINS
    CHOW, YL
    JOSEPH, TC
    [J]. CHEMICAL COMMUNICATIONS, 1968, (11) : 604 - &
  • [10] SINGLET OXYGEN DIMOL-SENSITIZED LUMINESCENCE FROM THERMALLY GENERATED SINGLET OXYGEN
    FU, YL
    KRASNOVSKY, AA
    FOOTE, CS
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (22) : 10282 - 10285